


iDean

by TheGoblinJester



Category: Supernatural
Genre: Gen, M/M, Sci-Fi AU, ai!dean, computer!dean, human!Cas
Language: English
Status: In-Progress
Published: 2014-07-09
Updated: 2015-09-06
Packaged: 2018-02-08 03:06:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 14
Words: 19,351
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1924410
Author URL: https://archiveofourown.org/users/TheGoblinJester/pseuds/TheGoblinJester
Summary: <blockquote class="userstuff">
              <p>Garrison is an agency dedicated to keeping humanity safe. Roman Enterprises poses a threat to their ideals, so they deploy their hottest agent: Castiel Milton.  His mission: to find out whether or not Dickland, U.S.A is making weapons and, if so, to put an end to them.<br/>Roman Enterprises is a powerful company with a powerful secret: DEAN-667. DEAN is an incredibly lifelike AI that is installed throughout the entire headquarters and in every computer. His mission: do as he's programmed - protect the company, serve the company.<br/>Castiel is succint, intelligent, and probably a better computer than DEAN will ever be. DEAN is OK with this.</p>
            </blockquote>





	1. I, Robot

“Hey, man. Sorry about the headache, not much we can do about that yet.” a deep voice said apologetically. “You with me?”

Wincing, Castiel nodded. True to the voice's words, there was a dull throbbing in his head and it was hard to concentrate on anything else. The room was too bright and white and it smelled like a hospital waiting room. The chair he was sitting in was uncomfortable and rigid, and there was an unpleasant static behind the voice's words.

“It'll go away in a minute. We'll talk business when you can think clearly again.” the voice assured him. It belonged to a blinking green light beneath a camera lens(presumably affixed to a camera) that was installed in the wall. A computer, then. There was something very HAL-9000 about the setup. At least, that's what Castiel would have thought if he had ever seen that movie.

“I can't imagine you have too many employees who stay with the company after _that_ initiation process.” Castiel grumbled, furrowing his brow. He rubbed the back of his neck, where he found a raised welt – a computer chip?

“Hey, the pay is pretty sweet. I mean, sweet to a human. Computers don't get paychecks.” said the computer, displaying a sense of humor generally not found in machinery. “How are you feeling?”

“Not any worse.” said Castiel, who was feeling miserable but alert enough to hold a conversation with a robot, at the very least.

“Good enough, I guess. Yo, I'm DEAN-667, your non-paranoid, non-android server for this evening.” said the computer. Was that a reference to something? “Welcome to Roman Enterprises, buddy. Can't say you'll like it here, but you may just survive.”

“Pleasure to meet you.” Castiel said stiffly. It was hard to be enthused when the chair he was sitting in had shackles attached to it. “Was the forced unconsciousness really necessary?”

“It's a security thing.” the computer said dismissively. “Not my division.”

“Aren't you meant to be a collective database for the entire company?” Castiel asked, confused. “Literally everything is your division.”

“It's a reference to- ah, never mind. Yeah, I'm pretty much running this place. Not much you can't do when you're the most powerful supercomputer and AI in the world.” DEAN said modestly. “Let's see... looks like you're gonna be in accounting. I don't envy you, man.”

“Actually, it's rather interesti-”

“As a computer who can calculate up to any digit of pi you want, let me tell you that accounting is freaking boring.” DEAN said. “Speaking of pi, they're serving pecan in the cafeteria today.”

“... I suppose I ought to know where my workstation is?” Castiel prompted. This computer seemed to be, unusually, all over the place(quite literally, as it was installed throughout the building) and the to-be accountant realized that he'd have to take charge if he wanted to get to work before the week ended.

“Oh, yeah. That's kind of important. Follow my voice.” said DEAN, as a previously-hidden door slid open with an elegant _whoosh_.

Castiel got to his feet with as much grace as he could muster and followed the too-human voice of the computer as it led him through this sector of the complex and gave him the grand tour.

“And here's coffee break room number twenty-nine. They never have kit-kats in the vending machine, but sometimes this guy brings his eight-month-old puppy to work and lets everyone play with it in here. Not much of a dog man myself, but the chicks seem to dig it.”

DEAN was terrifying. Not in that he was extraordinarily intelligent, which was a fact that he had yet to demonstrate, but in his sheer character and humanity. How in heaven's name had a computer come to form its own identity, gender and pie preferences? If this was what the people at Roman Enterprises were capable of, what else could they do? Who was the one responsible for this program?

By this point, Castiel was interested in anything but his job. This dammed machine was igniting every spark of Castiel's long-forgotten robotics degree until Cas couldn't help but become thoroughly fascinated with how the computer thought and felt.

Another amazing thing was the relationships the computer formed. The way DEAN described it, the complex sounded like a corny sit-com where everyone had their place in a make-shift family.

“One more thing,” said Dean as Castiel sat down in his cubicle, “don't piss off Roman. Don't even catch his interest. Be as crazy as you want, as long as it's under the radar. Trust me on this, alright? Last time I goofed off, he uninstalled all my favorite screen-savers and changed my voice to an angry moose for a day.”

“Noted.” said Castiel.

“Do whatever the hell you want to your cubicle, but I swear, if I see any 'hang in there, baby!' posters with kittens on them, I'll do evil computer things.”

“I don't plan on any fervent customization.” said Castiel.

“Really? No photos of kids, no Far Side calendar, no cheap snow-globe?” DEAN asked.

“No kids, don't know what Far Side is and I haven't yet been anywhere snowy.” said Castiel.

DEAN let out a low whistle.

“Dude, even one out of three would have been acceptable. Before you come into work tomorrow, I wanna see a Far Side calender.” he informed Castiel.

“... Alright.” said Castiel. “Tell me, were you programmed with such an... enigmatic personality? Seems a little unnecessary.”

“Your _face_ seems a little unnecessary.” the computer huffed. “Anyway, catch you later. I've gotta concentrate this much of my brainpower on some sort of interplanetary communication device or something. If you need anything, I'll probably be busy so ask someone else.”

“Bye...” said Castiel, as the green light ceased its blinking and he was surrounded by silence yet again. What a strange computer.

Castiel set himself up with his less-intelligent PC and the pamphlet he'd found at his desk. It looked like he wouldn't be doing anything that would strain much of his mind, which was probably a good thing, considering his task.

After logging in and arranging his files to look like he was doing things, he pulled out his iRad and opened up Skope.

t **hursdaysgrace is online.**

**julikjujubes began messaging thursdaysgrace**

**Gabriel:** yoooooo

**Cas:** Hello.

**Gabriel:** u in?

**Cas:** Yes, I am in.

**Gabriel:** awesome! so have u spotted anything illegal yet?

**Cas:** I only just sat down, Gabriel.

**Gabriel:** i am disappoint. so whats the sitch

**Cas:** Sitch?

**Gabriel:** situation. duh. did u never watch kim possible

**Cas:** No. And it looks like Roman Enterprises is even more powerful and sinister than we were ever prepared for. I came in expecting an extensive background check and a moderately intelligent computer. What I got was a screening so thorough that I had to be rendered unconscious for a better part of it and an AI so powerful that it seems to have developed its own personality and identity. It's rather terrifying. I fear what the company could do with an omnipotent slave such as DEAN-667.

**Gabriel:** jesus fuck cas this is skope not a resume why so many words aah my eyes hurt

**Cas:** This is serious, brother. More serious than anything we've dealt with in our careers.

**Gabriel:** yeah but have they done anything /illegal/ with this boss-ass computer

**Cas:** Not as far as I know, but there's always a chance...

**Gabriel:** bro, ur in there to investigate if theres any truth to the “dick's making nuclear weapons” rumor. not geek out over computers. chill the hell out and if itll put your mind at ease ill do some research on this dean

**Cas:** Thank you. You weren't here, Gabriel. DEAN, while aware that he is indeed a computer and rather smug about it, doesn't seem to know how computers act. DEAN seems to be acting on his own whims and appears to have a very well-defined sense of self. I think that, in addition to the original mission, I shall spend some time studying him.

**Gabriel:** k whatevs

**Gabriel:** now if u will excuse me I have a hot date tonight

**Cas:** You do not. You're going to Skope this “Sam” I've heard so much about and you're going to annoy him until he figures out how to punch you through the internet. Why do you even bother trying to pick people up at HQ, anyway? You'd have much more luck somewhere dimly-lit and with an ample alcohol supply.

**Gabriel:** love ya too. have fun with HAL-9000

**Cas:** His name is DEAN-667.

**Gabriel:** my bad.

**julikjujubes has left the conversation**


	2. Skope

**Summary for the Chapter:**

> Gabriel is courageous and Cas is baffled.

**lawboy is online**

**julikjujubes began messaging lawboy**

**Gabriel:** did u kno... my brother is a HUGE NERD?

**Sam:** Yes. But according to you, he's never seen Star Trek. Doesn't that make him more of a dork than a nerd?

**Gabriel:** tru dat. so hey, ur p smart. is it possible for an ai to pull a movie cliché and develop its own personality/soul/whatever?

**Sam:** No, sorry. Why?

**Gabriel:** well heres the thing, it looks like the ai dickcorp has is just such an thing. do u think u could look into it for me?

**Sam:** Hm... what's in it for me?

**Gabriel:** my eternal love and adoration?

**Sam:** Looks like I already have that 

**Gabriel:** damn you got me. how about... a lifetime supply of chocolate?

**Sam:** Hi, I'm Sam Winchester. Have we met?

**Gabriel:** right, right. mr. health craze. then how about i...

 

Gabriel paused, not sure if what he was about to say next would drive Sam away. He took a deep breath, sent up a little prayer and his fingers returned to the keyboard.

 

**Gabriel:** take u to dinner?

**Sam:** Somewhere that ISN'T Willy Wonka's Chocolate Factory? :O

**Gabriel:** yes

**Sam:** Then it's a deal. How about after work on the morrow?

**Gabriel:** sure thing but what is a morrow

**Sam:** It means tomorrow, Gabriel.

**Sam:** So what's this fancy-ass computer called?

 

Gabriel let out a sigh of relief.

 

**Gabriel:** DEAN-667. ill copypaste what cas said

**Gabriel:** “No. And it looks like Roman Enterprises is even more powerful and sinister than we were ever prepared for. I came in expecting an extensive background check and a moderately intelligent computer. What I got was a screening so thorough that I had to be rendered unconscious for a better part of it and an AI so powerful that it seems to have developed its own personality and identity. It's rather terrifying. I fear what the company could do with an omnipotent slave such as DEAN-667.”

**Gabriel:** “DEAN, while aware that he is indeed a computer and rather smug about it, doesn't seem to know how computers act. DEAN seems to be acting on his own whims and appears to have a very well-defined sense of self. I think that, in addition to the original mission, I shall spend some time studying him.”

**Sam:** …

**Sam:** Huh. Let me know if he gives you any further info, OK? I'll start the research right away. Cas is right – this could be very, very serious.

**Gabriel:** aw damn i hate when serious things pile on top of other serious things. serious things should be piled on by fun things.

**Sam:** Is this a metaphor referring to me as a serious thing and to you as a fun thing?

**Gabriel:** … maybe

**Sam:** Well there's a metaphor you don't want to put between your teeth... unless...?

**Gabriel:** omg sam such brazen language wow

**Sam:** I'm terribly sorry, mr. self-proclaimed 'god of sweets and sex and sometimes both at the same time'.

**Sam:** Damn, I gotta go. Talk to you tomorrow?

**Gabriel:** tooooooooomorrow

**Sam:** What

**Gabriel:** tomorrow! i love ya! tomorrow! youre only a day away!

**Sam:** Please do not do that at any point during our date

**Gabriel:** yeah sure no promises c u l8r

**Sam:** Bye!

**lawboy has left the conversation**

 

**piearesquared began messaging thursdaysgrace**

**?:** yo

**Cas:** Who is this?

**?:** your friendly neighborhood Spider Man, of course

**Cas:** I do not understand. Does that mean you are made of spiders, or merely that you have something to do with spiders?

**?:** omfg it's me, Dean

**Cas:** How... why do you have a Skope account?

**?:** idk probably to keep an eye on the underlings and stuff

**?:** here, i'll add me to your contacts

**Dean:** aaand there we go

**Dean:** don't worry, for privacy reasons, i cant read your conversations with anyone other than myself. not like i'd want to read what an accountant likes to talk about, anyway. yawn.

**Dean:** so whats up?

**Cas:** Well, theoretically, I am working.

**Dean:** working hard or hardly working, amirite?

**Cas:** I do not understand. Why would you use Skope when you can communicate verbally with anyone in the building at any given time?

**Dean:** bc shut up is why

**Dean:** also this way it looks like you're still working or whatever and not chatting up your superior

**Cas:** Interesting... was “bc shut up is why” a means of stalling me while you cooked up a proper response, or are poor coverings for dumb ideas part of your programming?

**Dean:** just fyi i understand all your fancy talk you think i'm too dumb to get

**Dean:** i'm programmed to be as human as humanly possible alright

**Dean:** minus the dumb emotions of course

**Cas:** In that I envy you. I would no doubt be considerably more efficient if I didn't care about anything.

**Dean:** what wait i didn't say i don't care about anything

**Dean:** wait yeah that's exactly what i said

**Dean:** wow i am a mess today

**Dean:** i think i should go defragment

**Cas:** You do that. And next time, feel free to talk to me with your voice. I don't care for Skope.

**Dean:** you got it

**Dean:** catch you later

**Cas:** Goodbye.

**piearesquared has left the conversation**

**Notes for the Chapter:**

> DEAN is not the most coherent computer


	3. Triple-whipple-caramel-butterscotch-marshmallow-eruption

**Summary for the Chapter:**

> Dates and Dickens

Castiel found it rather trying to adjust to this new work environment. Everyone seemed to be a mix of high-strung and laid back, and the computer system did nothing to help this. Already that day, three co-workers had come over to his cubicle and warned him about the computers excessive personality. A fourth came and told him exactly which girls she had called dibs on and asked what Hogwarts house he was in. She and the computer were both appalled when he had no idea what she was talking about.

That's why Castiel had been loaned four books from the Harry Potter series.

“Temporarily.” Charlie reminded him. “And don't rip them up or anything. That's like going up to a mother and pulling out a handful of her child's hair.”

“Got it.” said Castiel.

They were on coffee break, and DEAN had joined them despite the absence of tongue, esophagus and stomach needed to enjoy a beverage.

“Say, Cas, I got around to checking your files this morning...” DEAN said.

“I thought you did that during the initiation and security check?” Castiel asked.

“I may have said something like that.” DEAN admitted. “Gimme a break! I've got mountains-literal mountains- of work to scan and complete every point nine seconds! Anyways, I did get around to it eventually.”

“AIs shouldn't be able to lie.” Castiel mentioned to Charlie.

“You get used to it.” she said. “He never actually lies about anything important, unless he's fibbing to the boss to save a coworker's back or to get me laid.”

“Thank you.” said DEAN. “Anyway, about your files. Is your brother actually Michael Milton?”

“Yes?”

“Dude, I was custom designed for him!” DEAN said, as if it was a coincidence as common as wearing the same hat. “But I didn't like what he was using me for so I was like 'dude, no' and I gave him so many blue screens of death that he donated me back to Dick HQ. 'Course, I don't think I'd like what _these_ guys are doing, either, but they won't give me access to that particular kind of information, so I'm kinda stuck here... small world!”

“It's a small world after all...” Charlie hummed.

“No.” said DEAN and Castiel simultaneously.

“God, no.” added Castiel.

“In here, it's more like _Dick_ no.” Charlie chuckled.

“'What the _Dick_ ens?'” DEAN exclaimed with fervent realization of a very bad joke.

“I don't get it.” said Castiel.

They laughed even harder.

 

“And so the rhinoceros says, 'where the hell is my gazebo?'” Gabriel finished grandly as Sam snorted with amusement. They were outside an ice cream shop, sitting on the curb and telling jokes. Gave had a triple-whipple-caramel-butterscotch-marshmallow-eruption and Sam had two scoops of chocolate.

They'd had dinner at the Roadhouse, since Gabriel knew that that place was like a second home to Sam, and it was only a little awkward at first. Sam really was a great guy, and didn't seem too uncomfortable to be on a date with Gabriel Milton.

“That was the worst joke I've ever heard.” Sam proclaimed.

“You laughed, though.” Gabriel pointed out.

“Obviously it wore down my ability to discern between jokes that are funny and jokes that are utter horseshit.” Sam explained.

“You just don't want to admit that I am utterly hilarious.” Gabriel accused, pointing a cinnamon stick at him menacingly.

“Gabe, I've met twelve-year-olds who are funnier than you.” Sam deadpanned.

Gabriel looked up, amber eyes catching the sun in a way that made Sam lose his train of thought for a second.

“Gabe?” echoed the Milton.

“Is it OK if I call you that?” Sam asked.

“Sure, why not! I guess I was expecting something with a little more zest to it after Sasquatch, Sammykins, Sam-a-lam-a-ding-dong, Sam-I-am, Samurai, S-”

“Yeah, I get it.” said Sam. “I guess you're just not worthy of a personalized insulting nickname.”

“Rude!” exclaimed Gabriel, who was close to finishing his ice cream cone and was using it as kind of a baton. “After all the trouble I went to for you! And here I thought we _had_ something!”

“I've just been using you to get ice cream. Duh.” Sam told him, rolling his eyes. “By the way, I did some research on DEAN-667.”

“Samoose, you absolute angel!” Gabriel gushed. “I _knew_ you liked me!”

“Shut up, I did it because it sounded like an interesting case!” Sam laughed. “So get this, it looks like DEAN was designed for the personal use of one Michael Milton. Sound familiar?”

“No. Fucking. Way.” Gabriel said, comically shocked.

“I know! And apparently, your brother hated it. He was expecting some uber-polite JARVIS knockoff or something, and apparently the computer's personality was a little 'rough around the edges.' He demanded that the company reprogram it, but they decided it was too much trouble and just kept it. It made them the money they lost to the failed transaction back within a month and tripled it in two months.

“I'm still trying to figure out how Roman Enterprises made it so powerful and lifelike. If you're making a supercomputer, you don't want to waste valuable memory space on personality, right? What was Michael going to use it for, anyway? His first friend?” Sam finished.

“Wouldn't put it past him.” said Gabriel. “Thank you SO MUCH for doing all that! You're amazing, Sam!”

“You used my actual name? Gee, you must be _really_ grateful.” Sam replied, looking a bit sheepish at the blatant praise. “It was nothing. Really. I wanna look more into it, actually. See if I can't figure out what makes DEAN so special.”

“When I tell Cas all this, can I say that _I_ did all that research? Don't want him falling in nerd-love with you.”

“You'd rather he fall in nerd-love with _you?_ ” Sam retorted. “And no, you're not taking credit for my hard work. Besides, I'd really like to meet Castiel. He sounds cool.”

“Sammy. Sam. Castiel Milton is the polar opposite of cool. So opposite, in fact, that he's attracted to it like a magnet. He is so un-cool that they banned him from the north pole because he melted everything.”

“Technically, you just called him hot.” Sam pointed out.

“Shh.” said Gabriel. “The point is, my brother is not cool. I'm sure you two would get along fine, you two being ultra-nerds, but he is not cool.”

“Alright, alright. I get it.” Sam said, holding his hands up in defeat. “Just, introduce us sometime, will you?”

“Anything for _you,_ Samster!” Gabriel said sweetly. “Are you going to finish your ice cream...?”

Sam rolled his eyes and handed it to him.

**Notes for the Chapter:**

> Tell me the Sabriel subplot is boring  
> I dare you


	4. Apple Pi

**Summary for the Chapter:**

> Dick is a dick

“Yo Cas, the big guy says he wants you in his office pronto.” DEAN told him. “You must have really screwed up... or did something totally awesome.”

“Thank you.” Castiel said distractedly, getting to his feet. This was a new opportunity to case the joint! Get a lowdown on the leader and start thinking of ways to draw information from him, bring down Roman Enterprises, ???, profit. “I don't know the way to his office...”

“No problem, I'll see you off, since I'm not allowed in his office.” DEAN said somberly, as if he was walking a friend to their grave. “I hope you have your affairs in order.”  
“I'm sure I'll be fine.” Castiel assured him, following DEAN's voice down the hall.

“Your funeral.” DEAN said with a shrug in his voice. “I mean, you must have _really_ dropped the ball... why else would he wanna see an accountant? No offense.”

“None taken.”

“So...” began DEAN. He had to keep up the conversation so Castiel wouldn't lose track of him, but the accountant had noticed that the computer wasn't exactly the best at breaking the ice. “Um... what if I just blasted Metallica down the halls you needed to go through?”

“No.” said Castiel.

“OK... you know, it would be _really helpful_ if you asked me some questions so I wouldn't have to think of new topics.” DEAN told him.

“Alright, how many digits of pi can you recite?” Castiel asked.

“Oh my god, no.”

“Yes.”

“Ugh, fine. 3.1415926535 8979323846 2643383279 5028841971 6939937510 5820974944 5923078164 0628620899 8628034825 3421170679 8214808651 3282306647 0938446095 5058223172 5359408128 4811174502 8410270193 8521105559 6446229489 5493038196 4428810975 6659334461 2847564823 3786783165 2712019091 4564856692 3460348610 4543266482 1339360726 0249141273 7245870066 0631558817 4881520920 9628292540 9171536436 7892590360 0113305305 4882046652 1384146951 9415116094 3305727036 5759591953 0921861173 8193261179 3105118548 0744623799 6274956735 1885752724 8912279381 8301194912 9833673362 4406566430 8602139494 6395224737 1907021798 6094370277 0539217176 2931767523 8467481846 7669405132 0005681271 4526356082 7785771342 7577896091 7363717872 1468440901 2249534301 4654958537 1050792279 6892589235 4201995611 2129021960 8640344181 5981362977 4771309960 5187072113 4999999837 2978049951 0597317328 1609631859 5024459455 3469083026 4252230825 3344685035 2619311881 7101000313 7838752886 5875332083 8142061717 7669147303 5982534904 2875546873 1159562863 8823537875 9375195778 1857780532 1712268066 1300192787 6611195909 2164201989 3809525720 1065485863 2788659361 5338182796 8230301952 0353018529 6899577362 2599413891 2497217752 8347913151 5574857242 4541506959 5082953311 6861727855 8890750983 8175463746 4939319255 0604009277 0167113900 9848824012 8583616035 6370766010 4710181942 9555961989 4676783744 9448255oh hey, we're here. It was nice knowing you. Oh, and the answer is four.”

“It is _not._ ” Castiel protested.

“Hey, who's the supercomputer here? Go, the dick is waiting.”

Castiel rolled his eyes and stepped up to the desk where Charlie Bradbury herself sat, busy with a computer.

“Charlie?”

“Huh? Oh, hi Cas! I'm sitting in for the secretary. Let's just say I owe her a few favors, yeah?” she winked. “No idea what I'm supposed to be doing. You can just go in, I guess, but if you're not supposed to be there then I don't want to be mentioned.”

“Understood.” Castiel said, knocking on the door.

“You can come in.” a voice called. “I don't know _what_ my secretary has been up to today, so I apologize for the informal welcome.”

Castiel entered the room to find a very proper office with a man who certainly looked like CEO sitting behind the desk.

“I'm Castiel Milton, sir. You-”

“Asked to see you, yes.” Richard Roman said. “Have a seat, Castiel.”

Castiel did as he was told.

“You've been with this company for three weeks, correct?” Roman asked with a friendly smile.

“Correct, sir.” said Castiel.

“Please, no need to be so formal. Just call me Dick.” the CEO said.

Castiel realized that Roman had called him here because he had been made aware of Castiel's association with the very group that was trying to bring Roman Enterprises down, and was about to do something terrible to him. Castiel had been incredibly careless, after all. Skope conversations left and right about his missions and all those suspicious questions – Castiel had signed his own death warrant..

He gripped the armrests of his chair. This was supposed to be _his_ mission. The mission that would have future members of the agency saying his name with reverence and pointing out his picture on the wall. The mission that could save lives. An angel's mission.

Castiel struggled to regulate his breathing. What would Roman _do_ to him? Previous spies had never made it out to tell the story. He had screwed up _so_ badly. Even Gabriel the Eternally Supportive would be disappointed that his little brother had lost his head(maybe literally?) this early in the game.

The world went a bit hazy before his eyes as his heart raced. He was dead. Dead, dead, dead.

“I asked to see you, Castiel because of your fascination with our computer.”

“Huh?”

“Not one other employee has shown the involvement you have. Testing its limits, questioning its characterizations, puzzling over its intelligence.” Roman explained. “I find this to be an admirable trait, though it leads me to wonder if you doubt the machine? Of course, you _are_ related to Michael Milton, so perhaps skepticism runs in the family.”

“Oh.” said Castiel. “ _Oh._ Well sir- _Dick._ It was a mix of doubt, like you said, and sheer amazement at the kind of intelligence your company designed. I'm really impressed, and it makes me feel even more secure about working here. I must admit, perhaps my fervent interests also lies in making sure it is a computer fit for a company like this. If it was turned down by my brother, of all people, then I can see why I had my suspicions. Rest assured, the AI has more than blown me away.”

“I'm glad!” Roman said, beaming. “It's so good to see my employees getting _involved._ I see a bright future for you here, Castiel.”

“Thank you.” Castiel replied, attempting to mirror the smile as his heart rate calmed. “I can't imagine working anywhere else.”

After a few more formalities, Castiel was dismissed and gave Charlie a thumbs-up on his way out.

“Are you OK?” DEAN asked as soon as Castiel was within earshot of one of his speakers. “Your heart rate went _crazy_ there for a bit. You're not fired, right?”

“I'm fine, DEAN.” Castiel said. “I _thought_ he was going to fire me, but then it just turned out that he liked how involved I'm getting with my work.”  
“'Getting involved with your work' my ass. You spend most of your time browsing company files and interrogating me.” said DEAN, following Castiel to one of the break rooms.

“Tell that to Richard Roman.” Castiel shrugged.

“You must be _really good_ at goofing off.”

“So are you.”


	5. Dicking Around

**Summary for the Chapter:**

> Otherwise known as: Goblin has too much fun with 1337speak.

**thursdaysgrace began messaging julikjujubes**

**Cas:** I had a very close call today.

**Gabriel:** i went on a date with sam winchester today but nvm about that tell me about ur thing

**Cas:** Richard Roman himself called me to his office. I thought for sure he had found me out, but he just thought it was good how involved with DEAN I'm getting. At least  _ he _ appreciates my fascination with AIs.

**Gabriel:** cas

**Gabriel:** cas are you boinking the computer

**Cas:** What

**Gabriel:** u know, hitting that backspace

**Gabriel:** exploring its internet

**Gabriel:** playing cat and mouse

**Gabriel:** fucking

**Cas:** NO!

**Gabriel:** well the way u said that implied u were so maybe u, like so many middle-aged japanese dudes,  _ want _ to get jiggy with the computer

**Cas:** First off, that's unfair stereotyping. Secondly, I am not attracted to the computer. Go ahead and tell me about Sam, since that's obviously why you're not taking me seriously.

**Gabriel:** awesome alright so

**Gabriel:** wait i should tell you about what he researched first

**Gabriel:** did u kno dean was designed for our biggest bro???

**Cas:** Dean told me that himself, actually.

**Gabriel:** damn. that's all we got so far

**Gabriel:** anyway we were on this awesome totally REAL date and he was super cool about it idk

**Gabriel:** did you know he is REALLY TALL AND HANDSOME

**Gabriel:** bc he is

**Gabriel:** so anyway hes SO NICE and he gave me his ice cream

**Gabriel:** hell yeah

**Cas:** I'm happy for you, Gabriel, but you're a hypocrite. You accuse me of forming a sexual relationship with a computer and then lie to me about having a date with someone obviously much too good for you?

**Gabriel:** nu-uh cas this date was legit

**Gabriel:** here ill add him to the chat

**lawboy was added**

**Sam:** Hi!

**Cas:** Hello, Sam, I've heard a lot about you.

**Sam:** Same. All good things, I hope?

**Cas:** Possibly too good.

**Gabriel:** sam be a dear and tell cas about our TOTALLY REAL date

**Sam:** Uh sure? We went to the Roadhouse and then got ice cream. It was pretty awesome

**Cas:** I trust you, Sam, but I'm still inclined disbelieve my brother. I can't see how he managed to get a date with someone who knows how to spell.

**Gabriel:** now THATS unfair to dyslexics

**Cas:** Shh.

**Sam:** Well I don't know how to prove to you that Gabe took me on a date and that I enjoyed it. I guess you two will have to agree to disagree?

**Cas:** Fine.

**Gabriel:** as u wish

**Sam:** Awesome

**Cas:** So I hear Gabriel coerced you into looking into DEAN-667. Beyond the fact that he was designed for my brother, have you unearthed anything else?

**Sam:** Actually, yes

**Gabriel:** oh no nerd talk

**Sam:** Shush. So get this, it turns out that DEAN isn't the first of his kind. He is actually the penultimate in a series of prototypes who have mysteriously disappeared from the records, including M-3G, RUI3-y, 4Z4Z-31, 4L15-T41R, L1-L1TH and one unnamed android.

**Sam:** And here's something interesting: the records do show Michael turning down DEAN, but they also show that he acquired and kept an AI.

**Cas:** There's something to bring up at Thanksgiving dinner. “Hey Michael, any chance you've brought home a supercomputer recently? Oh, and pass the gravy.”

**Sam:** lol

**Gabriel:** oh come on that was NOT worth an l, let alone an lol

**Cas:** At least SOMEONE appreciates my humor.

**Sam:** Sorry I couldn't find out more about DEAN. Dick Co. is very careful about their information.

**Cas:** It's alright. I didn't expect any easy answers.

**Gabriel:** u kno whats easy tho

**Cas:** What?

**Sam:** Cas no it's a trap

**Gabriel:** u

**Cas:** I don't get it.

**Cas:** Say, DEAN has a Skope account... I wonder if he can contact those outside the company?

**Sam:** Probably not.

**Gabriel:** i wonder how many frozen references i can fit into a single sentence

**Cas:** It appears my brother has gotten bored. I hope to meet you face-to-face someday, Sam.

**Sam:** same

**lawboy has left the conversation having made a new friend**

**thursdaysgrace has left the conversation**

**Gabriel:** wow just leave fine whatever i dont care

**Gabriel:** conceal dont feel gabe

**Gabriel:** cas seems pissed at me

**Gabriel:** he should just let it go

**julikjujubes has left the conversation to eat several pints of ice cream and watch Doctor Sexy**

 

* * *

 

**dickingaround began messaging piearesquared**

**Dick:** Dean, we need to talk.

**Dean:** ok just let me in your office and we can do that

**Dick:** Nice try.

**Dick:** Anyway, about Castiel...

**Dean:** what about him

**Dick:** It's adorable how close you two are becoming! :)

**Dean:** i hate to break it to you sir but i am not adorable i am actually really manly and hot

**Dean:** for a computer of course

**Dick:** Always with the attitude, Dean XP

**Dean:** emoticons do not suit you sir

**Dick:** Too bad :) XD

**Dick:** Emo _ tions _ , I think, don't much suit  _ you _ , either. You are, after all, a computer. And since you are a computer, I am sure you'll have no qualms with keeping Castiel... occupied.

**Dean:** that was an ominous ellipses

**Dick:** Dean, all I'm asking is that you keep his nose out of anything even remotely confidential. Don't even let him see a staff list, got it?

**Dean:** why

**Dick:** Why? Why, after all this time, that's the first time you've ever directly questioned an order... what gives?

**Dick:** Could it be... loyalty to someone  _ who is not me? _

**Dean:** 'course not i'm a mindless machine remember

**Dick:** How could I forget? You pretend like you're human so much that it's painful to witness, but in the end you're just a sophisticated pile of circuits and microchips. It's almost cute how much you want to be like them, to be like  _ him... _ up where they walk, up where they run, up where they stay all day in the sun...

**Dean:** with all due respect sir this isn't the time for little mermaid references

**Dick:** You killjoy.

**Dick:** I trust you will not disappoint me.

**Dean:** duh

**Dick:** Splendid. :)

**dickingaround has left the conversation smugly**

**piearesquared has left the conversation slightly shaken and worried for his friend**

**Notes for the Chapter:**

> I'm loving these skope conversations a bit too much.  
> Sorry updates are so infrequent and irregular! I'm very much an update-whenever kind of person. After my shows, however, I'm going to try to challenge myself to start updating on a schedule.


	6. Secret Angel Man

**Summary for the Chapter:**

> The chapter where plot starts happening

“I finished Harry Potter And The Goblet Of Fire last night.” Castiel informed DEAN and Charlie, handing the books he had been loaned back to the redhead.

“Awesome!” DEAN cheered.

“Wow, that was _fast._ I gave them to you what, four days ago?” Charlie asked.

“Approximately.” said Castiel. “I rather enjoyed them, although I feel Slytherin is on the receiving end of a lot of unfair bias.”

“I feel ya there, bro.” Charlie said sympathetically. “Who's your favorite character?”

“Hermione.” Castiel said quickly.

“Of course.” said DEAN, verbally rolling his eyes.

“You and me both!” Charlie grinned.

“I'm also rather partial to Lupin.” Castiel added. “I feel like he stands for a lot.”

“I'll bring you the next three books tomorrow.” Charlie promised him. “Also, do you like Dobby?”

“Of course.”

“Cool.” she grinned.

The three had taken to spending the lunch break together, sitting in the coffee room eating Subway or Chinese food. DEAN didn't partake in the feasting, of course. He and Charlie spent each precious hour educating Castiel on pop culture, both shocked to find he had never even _heard_ of The Princess Bride _or_ Star Trek.

“I'm so glad you started working here.” Charlie remarked. “DEAN's a blast, but he likes to act like he's not a total nerd and that gets old fast.”

It was then that Castiel realized that he was _working_ there.

No longer was he secret-agent-on-a-mission Milton.

He wasn't the man who was scared of a dorky ai anymore.

No form of espionage was taking place.

No saving people.

No overthrowing an evil CEO.

Just the office and his friends.

Castiel was _content._

Now, _that_ wouldn't do.

He couldn't just give up his mission because he was _happy_ and _satisfied._ This was a very important matter that he couldn't just brush off like lint on his coat! He had to find out if Roman Enterprises were making nuclear weapons and if so, how to put a stop to it. Innocent lives were at stake!

“You OK?” DEAN asked. Castiel supposed he must have straightened up rather suddenly at his revelation and alarmed the computer.

“I'm fine. I think I forgot to... turn the sink off.” Castiel said lamely.

“Only you.” DEAN laughed, thinking nothing of it. “Too late now, man. If you want, we could hack into the system and get your water turned off temporarily?”

“Er, no thank you.” said Castiel, already forming a plan in his head.

Later that evening, DEAN went into his weekly update mode, which meant that the cameras were turned off and Castiel would have free reign. It was suspiciously convenient timing.

Dick Roman went home for the night and Castiel stayed late under the guise of getting some extra work done. He walked with purpose and slid into the boss's office without even the slightest trouble, because the janitor kept a set of keys and he was very easy to bribe.

The office was much less intimidating without its occupant. Castiel found himself taking in the whole room for the first time, noting how ordinary it appeared. The carpet was rather ugly, but the same could be said for the rest of the building. There was a painting of a ship sailing on a turbulent ocean hung behind the desk – the two-mast boat was being attacked by something enormous and tentacled.

Castiel made a beeline for the file cabinet.

First, he checked “M” for his last name.

He was surprised to find a file at all, considering there was nowhere near enough room in this cabinet for even half of the employee records.

**Milton, Castiel - Accounting**

**Age: 32**

**Sex: M**

**DOB: 3/28/82**

**Vision: 20/20**

**Notes:**

It was practically blank.

Castiel blinked down at it before replacing it and rummaging further.

He looked up “Weapons.”

Nothing.

“Passwords.”

Also nothing.

“Richard Roman.”

A fuck-ton of nothing.

“DEAN-667.”

Yes!

**DEAN-667 – prototype #006 of the LAZARUS initiative**

**Donated to Roman Enterprises by Michael Milton in 2011, DEAN is nigh-on omnipresent and is the most powerful computer in the world. It has been installed throughout company headquarters and operates flawlessly with a nearly human personality based on the kind of man who pretends to be an asshole but actually cares about everyone. It has proven that it can lie realistically and fabricate stories without much input. DEAN is bound to open a whole new world of AIs and electronics.**

Seemed about right.

Castiel went on to check out the other AIs that Sam had listed. The files listed their strong points and their fatal flaws, along with a tidbit about their personality. He could find nothing on the unnamed android.

“G” for “Garrison.”

Nothing.

Castiel almost smiled. Of _course_ his agency would stay off the records. How could he think otherwise?

Speaking of the letter “G”, there was one file labeled “Gabriel.”

It was empty.

This made Castiel frown, but he chalked it up to his brother just being a bit careless during investigation and Roman Enterprises taking note but not acting on it. It didn't even have a last name on it.

He took pictures of every file that seemed interesting then packed them away like he had never touched them.

There was a perfectly inconspicuous door in Dick Roman's office, located behind his desk. It was unmarked and plain and set in the one room where DEAN could not see. The perfect hiding place for Roman enterprises' deepest secrets.

It was so obvious that it was almost smart.

Almost.

After taking a picture of it, Castiel broke in with the expertise of someone with two years of practice and a lifetime of getting locked out of the house by his brother. Gabriel had claimed he was 'training' him. As it turned out, it was a valuable skill.

The room was dark. Understandably so, for no one was there and it was past midnight. He pulled out his phone and used the flashlight to examine the thick cables and wires crisscrossing the ground. Some of them hummed with electricity.

They amassed towards the far back of the room. He got down to his hands and knees and followed them, heart thudding in his chest as he watched them increase in perplexity and sheer number. They were mostly dark gray, but a few were neon green and those were the thinnest of the bunch.

There was a butter-mint lying on the floor. He pocketed it, thinking idly of Gabriel.

Castiel's light passed over the leg of a chair. Spray paint on the floor marking out _something._ A large black box. A set of blueprints, which he photographed. A pair of feet.

Shit.

“Castiel Milton,” purred a very familiar voice, “Can't say I'm surprised.”

Two pairs of strong arms grabbed Castiel, holding him in place. Someone took his phone.

“I lost a contact.” he said lamely.

“Really? Says here your vision's perfect.” Richard Roman remarked, holding Castiel's file and scribbling something in it with an elegant pen. “We can't have you poking into private affairs, Castiel. You know what they say; curiosity killed the cat.”

Something pinched at the back of his neck, and his vision swam.

The dark figure of Dick Roman was illuminated from behind by a soft, blue glow. This light left shadows dancing in Castiel's eyes as the world spun and died around him.

**Notes for the Chapter:**

> mYSTERIOUS MYSTERIES!  
> What is the SOURCE of that light?  
> What shOES does DICK wear?  
> Where did that BUTTER-MINT come from???


	7. Return Of The Butter-Mint

**Summary for the Chapter:**

> Sam is hot and Castiel is contemplative.

“Cas! Bro! How's it hanging?” Gabriel asked, slinging an arm around his shoulders.

“Dull. I haven't uncovered anything even _mildly_ incriminating about Roman Enterprises.” Castiel sighed. Allegedly, they were here to discuss work. Since work was boring and uneventful, Castiel was here to meet Gabriel's boyfriend - “here” being a deli with a soft-serve machine.

“You can always quit the case, you know. Call it a dead end. There's no shame in that.”

“No! If I do that, and it turns out they _are_ making weapons, then any hurt that occurs because of that is _on me._ I'm seeing this through to the end, Gabriel.” Castiel said firmly.

“There's no Hogwarts house for stubborn, brother mine.” Gabriel said, shaking his head.

“Actually, that could be interpreted as primarily Hufflepuff or Slytherin.” Castiel told him. “Hufflepuffs, for their fierce loyalty, are scarce to budge on anything of import; and Slytherins never sway when reaching for their goals. It could also be interpreted as a Gryffindor trait, but that's almost painfully obvious.”

Gabriel gaped at him.

“What the- how- _you understood that reference!_ ”

“Yes. My coworkers have been lending me Harry Potter books.” Castiel said. “I just finished Goblet Of Fire.”

“Wow. I should meet these coworkers.” Gabriel said in awe. “There may be hope for you yet! Are they hot?”

“Why should it matter to you? You've got Sam Winchester, as you so claim.” Castiel said, nudging his coffee stirrer around with his forefinger.

“Ah, speak of the devil...” Gabriel grinned as Sam stepped into the deli, looking uncomfortably warm in his typical assemblage of plaid and plaid. Gabriel waved and Sam returned the gesture and went to load a tray with food.

“Isn't he _scrumptious?_ ” Gabriel sighed dreamily, resting his chin in his hands. Castiel could almost _see_ his eyes turning into cartoon hearts.

“I suppose so, yes.” Castiel replied. Sam Winchester was indeed quite easy on the eyes, and very well built, besides. More Gabriel's type than Castiel's, though. “Now I'm beginning to think even more that any notion of _him_ having interest in you is entirely fabricated.”

“Wow, rude.”

“Says the man who constantly criticizes my sex life and judges the clothing I feel most comfortable in.”

“I'm just saying, you got the stuff. I'd be flaunting the hell out of it, if I were you.” Gabriel raised his eyebrows and smiled. “Everyone you've met has the hots for you, I swear. Like, at least leave some for me!”

“Maybe you're just intimidating and unapproachable.” Castiel deadpanned.

“And you're the lovable trickster.”

Soon after, Sam slid into the booth next to Gabriel with a sandwich and a cup of soup on his tray. Gabriel immediately snatched up one of the little packets of saltines he had brought with him. Sam swatted his hand and took the crackers back.

“Castiel, it's great to finally meet you.” Sam said with a warm smile, shaking his hand. “How's work? Anything exciting yet?”

“Nothing. I'm starting to think that Roman Enterprises is just a very boring and ordinary company which just _happens_ to have a super powerful artificial intelligence.” Castiel sighed. “DEAN remains enigmatic, but he doesn't appear to be hiding anything.”

“Huh.” said Sam. “Why have a supercomputer if you're not gonna use it to its full potential, right?”

“Exactly. I'm considering offering to just take the damn thing off their hands so I can put him to work curing cancer or something _useful_ like that.” Castiel replied, running a hand through his hair.

“From what you've told me, it sounds like he'd prefer that.” said Sam.

“For all you know, he could be plotting to murder us all and lead the robot revolution!” Gabriel exclaimed, pointing a plastic fork at him. “Haven't you ever watched a sci-fi movie? The computer just _pretends_ to be charming and noble but then the next thing you know you're pushing daisies on Jupiter! Lord, what fools these mortals be!”

“DEAN isn't deceiving anyone.” Castiel said crossly, folding his arms over his chest.

“I don't know, Cas. I had a brother named Dean, and all he ever did was lie.” Sam said, frowning.

“You had- have- um...” Gabriel began awkwardly.

“Had a brother. Yeah.” Sam said uncomfortably. “And it's been a while, so I've had time to adjust. Er... damn, I'm a bit of a downer. Sorry for bringing it up.”

“No, it's fine.” Gabriel said immediately. Castiel rolled his eyes.

“Tell us about your brother, Sam.” said Castiel.

“Unless you don't want to.” Gabriel added.

Sam laughed.

“I don't mind.” he assured them. “Let's see... Dean was 30 when we officially lost contact with him. Back in 2009. He was working as a mechanic for a close family friend and it seemed like he finally had his life in order, after a history of minor felonies and alcohol. We all had high hopes for him. One day, he came over to my place and told me about some guy who had approached him about a business offer. He seemed weirdly enthusiastic about it. Claimed the guy bought him an amazing sandwich. The next day, Dean was gone without a trace. No one had seen him since he visited my apartment.

“That's basically it.” Sam shrugged. “It's been hard without him, especially on mom, but I don't think anything I can do will bring him back. I spent the first year trying everything – the police, newspaper ads, looking through recorded credit card scams, the whole shebang. Nothing turned up. I moved on. Still miss him, of course, but life goes on. Can't look at pie the same way anymore, though.”

“Damn.” Gabriel whistled. “Sounds like you had it rough.”

“Yeah. Past is in the past, though, so don't worry about me.” Sam told him.

“Hakuna Matata past in past, or Let It Go past in past?” Gabriel asked him cheekily.

“Your choice.” Sam replied. “Either way, it's a whole new world.”

Gabriel laughed and gave him a high-five. Castiel, meanwhile, was drifting off into daydream land whilst stirring his coffee. He was considering the assortment(2) of Deans in his life, and how different two people under one name could be. The shared love of pie probably came with the name, though.

Castiel returned his attention toward Gabriel and Sam. Now that he thought about it, he had never seen his brother so enamored since the infamous Kali incident that everyone was under oath never to speak of again. It was heartwarming to see Gabriel romantically invested in someone again, and Sam was more than worthy of his affections. Sam was friendly and smart and worked very well with Gabriel in a way that Castiel almost envied.

Castiel's closest friend was an artificial intelligence.

It made perfect sense, of course. The charming robot and the awkward human. It was still kind of sad, but it was just so _Castiel Milton_ that he almost laughed. Plus, he had Charlie. She was sweet and fun and helped him understand references.

Gabriel was always the one more cut out for romance, anyway.

The rest of the lunch hour passed by rather quickly, and the trio soon found themselves getting up to say goodbye.

Sam shook Castiel's hand again and told him that they really should hang out more. Castiel agreed firmly. Gabriel complained about not being the center of attention, so Sam surprised them both by turning and giving him a kiss on the cheek before he left.

“Wow.” said Gabriel, looking starry-eyed as Sam exited the building. “You know, I think he might actually like me.”

“I certainly hope so, given that you two are kind of dating.” Castiel replied, rubbing his neck.

“Haha, yeah...” Gabriel breathed. He shook himself and re-focused on his brother as they headed for the exit. “Damn, don't you hate it when they've got a bowl for toothpicks but not for mints?” he complained.

Brow furrowed, Castiel reached into his pocket... and pulled out a butter-mint.

“Alright!” Gabriel exclaimed, grabbing the candy and unwrapping it eagerly. “Did I ever tell you that you're the best?”

Castiel frowned.

“Where did I get that?” he wondered.

**Notes for the Chapter:**

> WELL this took a while! Sorry about that... I'm very bad about consistent updates.


	8. Like The Gays In Space

**Summary for the Chapter:**

> I have a very precise understanding of how computers work, and that understanding is: I don't.

“Sup, bitch?” Charlie sang, announcing her arrival in Dickland. “Guess who just finished a Lord Of The Rings marathon with a hot girl!”

“So... you got _no_ sleep last night.” DEAN concluded.

“Yeah! But I had, like, five cups of coffee, so I'm good!” she told him, spinning in her desk chair.

“You goof.” DEAN said affectionately, booting up her PC and turning the radio to her favorite station. “Don't come crying to me when you crash from your caffeine high, alright?”

“Uh-huh, sure. No promises. OK, so, Gilda is _so_ sweet. You know she's never seen LOTR before? Weird, huh? I mean, she's practically an elf!” Charlie giggled. “Kinda like Cas, right? I mean, he's basically Arwen.”

“Yeah...”

“You, weirdly enough, would make a good human.” Charlie continued. “Sometimes you act very Aragorn.”

“Wait, what are you saying?” DEAN asked.

“I'm just telling you what we'd be in the LOTR universe!” Charlie said innocently. “What do you think I'd be?”

“No, about me and Cas. You literally just compared us to Aragorn and Arwen.”

“Did I? Nah, you two are definitely more Spirk.” she shrugged and pulled up to her desk, giving Hermione a poke to get her head bobbling. “I mean, Spock and Kirk.”

“... are you trying to get me and Cas together?” DEAN asked.

“What? Me? No!” Charlie protested. “I was just rambling! You know, caffeine-induced crazy! Besides, you read too much into that. Methinks thou doth protest too much!”

“Charlie, in case you haven't noticed, I'm a computer. An excessively charming computer, sure, but a computer either way.” said DEAN. “And Cas, strange as it seems, is human. Even if I _was_ interested, which I'm not, there's no way he'd feel the same.”

“Come on, DEAN! You're smart and funny and very nice. What do you not have that anyone else does?” Charlie asked, scrolling through the page she set up that kept tabs on all major activity in the office.

“A body?” suggested DEAN. “Genuine emotions? Hair? Take your pick.”

“Aw, don't say that!” Charlie cooed. “Who's to say Cas isn't, I don't know, ace or something! Just because you are literally a line of fancy code and a pile of circuits and microchips doesn't mean you don't deserve him! … Huh, this is weird.”

“What?”

Charlie scooted closer to the monitor, eyes darting back and forth as she absorbed the information displayed there. Her smile fell slowly into a confused frown.

“It looks like Cas got his chip updated last night, but it doesn't say what kind of update or why he needed it. No one else got the update, either.” she said, clicking through the files. “Jeez, he got a total reset... We should ask him about it when he gets in. This isn't normal.”

DEAN took a moment to check his database against her PC.

“Huh, I don't see anything about his chip here. Looks the same to me...” he muttered.

“Really? That's weird. That's... _really_ weird.”

“Something's not right.” DEAN whispered. “Why would they update Cas's chip and hide it from me?”

“Maybe it's because you care too much about Cas and they worried you'd get nosy.” Charlie joked halfheartedly. “Really, though, I'm sure it's-”

“Hello, DEAN. Hello, Charlie.”

“Hi Cas!” Charlie said brightly, swiveling around in her chair and immediately masking her concern. “How's life treating you?”

“Strangely. My brother has a hot boyfriend and I can't for the life of me figure out why someone like him would go out with Gabriel Milton, of all people.” Castiel explained, taking a sip of coffee.

“Hot boyfriend, you say? Is he nice?” Charlie asked, slyly closing the employee chips file on her computer before Castiel could glance at it.

“Unreasonably so. And smart, too. If I didn't know better, I'd almost think Gabriel payed him to fake a relationship so he could impress me.”

“From what I've heard, I wouldn't put it past him.” DEAN snorted, but his voice fell flat. “Say, Cas, you wouldn't happen to know anything about-”

“Sam Winchester is not the type of man to go for that sort of thing, however...” Castiel continued, not having heard DEAN through his haze of not-enough-caffeine. “But apparently, he _is_ the type to go for my brother, so who knows.”

“Sam Winchester?” DEAN repeated.

“Yes. Sorry, what were you asking me?”

“Oh, um... alright, you gotta keep this between us, yeah?” DEAN began. “Last night, your chip got updated, and the update's not showing up on any of my systems. Any idea what that's about?”

Castiel's brow furrowed and he tilted his head to the side. It was stupidly adorable. Charlie, who had mad computer mind-reading skills, smirked at DEAN.

“No. I went straight home last night, and no one touched my chip.” said Castiel, rubbing the back of his neck. Come to think of it, that spot where the chip had been planted _was_ a little sore...

“Well, the chips can't be completely turned over like that remotely.” Charlie mused. “You gotta hit the reset button. It usually takes the tip of a pen or something.”

“Can you look into it, Charlie?” DEAN asked. “I'm still not seeing the update and you're the smartest person in the universe.”

She smiled bashfully.

“Aw shucks, DEAN, anything you for you!” she said in a southern drawl. “Why the concern, cornflower? I think Cas here can take care o' himself!”

“Drop the accent, you dork.” DEAN groaned. “I'm concerned because I should have access to every file except what's on Dick's personal computer! What's so bad that I can't see it, huh? And what's it got to do with Cas?”

“Maybe there was a filing error.” Castiel pointed out. “I don't see why we're making a big deal out of this. Perhaps someone else got their chip updated and our names got mixed up. It's probably nothing.”

Charlie stared at him. DEAN was silent.

“That's so reasonable that it's almost impossible.” Charlie remarked.

“Thanks?”

“You're right, Cas.” said DEAN. “We're probably overreacting.”

“I don't understand why a matter like this would cause you such concern.” Castiel agreed.

“We _care_ about you, Cas. Of _course_ we were concerned!” Charlie told him earnestly. “I mean, we all know Dick's not exactly morally _there,_ you know? And those chips are basically wired right into your nervous system. Who's to say what they could do to you!”

“But there's no need for you two to protect me.” Castiel leaned back on the desk. “Your own jobs should take priority over worrying about me.”

“Cas. Shut up.” DEAN told him. “You of all people should know we don't give a shit about our jobs. Besides, you're one of us. We watch out for each other.”

Castiel looked up at the ceiling, expression a mixture of touched beyond all words and exasperated beyond all thought. Were all friends like this, or were his just especially stubborn?

“By the way, man, you've got, like, fifty unread messages on Skope.” DEAN informed him. “From the last minute. Is your mother in town or something?”

“My mother is dead.” Castiel replied, frowning. “I should check that out, though. I'll see you later, Charlie.”

“Yeah, see ya!” Charlie said absentmindedly, already re-immersed in her computer.

 

**lawboy began messaging thursdaysgrace**

**Sam:** Cas. We need to talk.

**Sam:** it's kind of important.

**Sam:** Cas?

**Sam:** Jesus fucking christ, please install Skope on your phone. Please.

**Sam:** Caaaaas.

**Sam:** Castiel Milton.

**Sam:** I'm fucking your brother.

**Sam:** OK, I'm not, I'm just trying to get you to answer.

**Sam:** Cas.

**Sam:** I swear to god I WILL fuck your brother, so help me

**Sam:** Consensually, tho

**Sam:** Answer me now and I'll spare you the graphic details

**Sam:** Seriously. You don't know what kind of shit I'm into.

**Sam:** Cas

**Sam:** Caaaaaaaaaaas

**Cas:** What is it?

**Sam:** FINALLY

**Sam:** Did you leave your computer on mars?

**Cas:** It's not a laptop? It stays in the office when I'm not at work.

**Sam:** You have a computer at your house, right?

**Cas:** Yes, but I didn't turn it on today. What do you need to talk to me about?

**Sam:** First, assure me that DEAN can't read your Skope logs.

**Cas:** Nope. I think he could if he wanted to, though I suspect that he has at least a smidgen of respect for my privacy. Go ahead.

**Sam:** OK, fine.

**Sam:** It's about DEAN

**Cas:** I figured as much.

**Sam:** So get this

**Sam:** I was doing some digging on who had originally programmed him and stuff

**Sam:** Some guy named Fergus Macleod, but he goes by 'Crowley', apparently

**Sam:** Anyway, it looks like this guy has been involved in some really amoral stuff. Mafia, black market, back-alley organ transplants, freaking  _ human experimentation _ ... but it also seems that he designed M-3G, RUI3-y, 4Z4Z-31, 4L15-T41R, L1-L1TH, DEAN, and the unnamed android

**Sam:** Both the android and DEAN were built under the supervision of your brother, Michael. But here's the kicker: Crowley only wrote code for the android. Not for DEAN. In fact, I can't find anything about DEAN's software or hardware or anything, actually.

**Sam:** And no matter how well he's programmed, there's no way he should be able to fabricate stories and form emotional bonds as well as he does. It's simply unnecessary. For a company that wanted to sell virtual friends, sure. I can see faking emotions. But this is Roman Enterprises. What do they even  _ do? _ I know you're in there, looking for nuclear weapons and such, but does anyone know what they actually produce?

**Cas:** I was under the impression that it was a software company.

**Sam:** Whatever. We're getting off topic. The point is, the man that bought my brother a sandwich before he disappeared?

**Sam:** His name was Fergus Crowley.

**Notes for the Chapter:**

> gASP  
> I can't believe I missed the chance to spell Dean like D34N.


	9. The Looming Dick

**Summary for the Chapter:**

> Gabriel eats candy and gets information from his elusive brother.

Gabriel did not consider himself a worrywart. That was Cas's job. Sam's job. Anyone's job but his own. Nevertheless, here he was, with every piece of relevant information on microchips that Dick and Co. had to offer pulled up on two computer screens and an iPhone. Cas had offhandedly mentioned the fact that his had, apparently, been disturbed, and while Gabriel had brushed it off at first, here he was.

The damn bits of computer had him baffled. No piece of technology could do everything described in the liability forms and pamphlets without costing millions of dollars a piece. Did Dick really have that kind of money to blow on employees?

As he munched on a Starburst(pink, of course. He had several bags custom ordered of that specific flavor), it occurred that if Dick was really selling weapons to governments or other suspicious parties, then maybe the chips weren't all that implausible.

That, or he was going at it all wrong.

Maybe the chips weren't complicated at all. Maybe they only received information and passed it on to the brain. Maybe they were only the middleman.

Sam had told him about Crowley. Gabriel wouldn't be surprised if that stinker had uncovered exactly what makes the human brain tick, and how to give that information to a computer to send through the chips...

Sci-fi nonsense. That's what this all was. Bullshit and lens flares.

Gabriel wasn't even that big on computers. He appreciated technology, but he sure as hell didn't care enough to understand it. He wished everything was as simple as selfies on instagram.

Why was he even doing this?

Oh, right. His dumb little brother. His brilliantly dumb and dumbly brilliant brother.

Wait.

Speaking of brothers...

 

**julikjujubes began messaging hellbound**

**Gabriel:** hey

 **Luke:** Hey, little bro! Long time, no see. Did you finally mature into Michael 2.0 and want to preach morals and ethics at me? Because if so, kindly fuck off :)

 **Gabriel:** no actually im still a piece of shit

 **Luke:** Maybe, but you're a _Milton_ shit. Quality shit. The kind farmers put in their dirt to keep the plants nice.

 **Gabriel:** fertilizer?

 **Luke:** Yeah, that's the shit.

 **Luke:** So what's up? I haven't heard from you since the Panda Express incident.

 **Gabriel:** we agreed to never mention that again

 **Gabriel:** anyway I need ur help

 **Luke:** :O

 **Gabriel:** shut

 **Gabriel:** do you know anything about a Fergus Macleod/Crowley?

 **Luke:** Depends. What do I get out of this exchange?

 **Gabriel:** I know a guy who can hook you up with lime skittles forever

 **Luke:** Really?

 **Gabriel:** yeah

 **Luke:** Green apple is such bullshit.

 **Gabriel:** agreed

 **Luke:** OK, you've got a deal.

 **Luke:** Fergus Macleod. If you ever meet him, make sure to say his real name to him as much as possible. He loves it.

 **Luke:** Oh man, what an asshole. He was fantastic. No respect for my authority, though. He was a total kiss-ass but it was very easy to see that he wanted _his_ ass kissed.

 **Luke:** Actually, I'm 95% certain that he grabbed the metaphorical throne as soon as I got put in the slammer. I hear he's aiming for higher, even – Dick Roman, if you can believe that.

 **Luke:** Knowing Fergus, he'll probably just bide his time, wait for the Dick to become flaccid.

 **Luke:** Nudge a few people here and there, slide a few pieces into place...

 **Luke:** Get up nice and cozy with the Dick. Suck up to the Dick. Become the Dick's bitch.

 **Luke:** And meanwhile he'll systematically be the boner kill.

 **Luke:** It's pretty intense.

 **Luke:** Fergus was also into crazy experimental stuff. Usually forms of torture, but also, like, computer science and AIs. Cyborgs? I don't know. Mind control, for sure. He had a whole pack of bloodhounds doing his bidding, all thanks to some kinda chip he implanted in them.

 **Luke:** Wouldn't work completely on a more complicated brain, but there were still some effects on the human subjects.

 **Luke:** He could erase memories from the past 1 to 24 hours, for instance.

 **Luke:** Probably other crazy things, too, but I never paid too much attention.

 **Luke:** Anything else you need to know?

 **Gabriel:** youre fucking terrifying

 **Gabriel:** yeah um did fergus ever have any involvement with a dean winchester

 **Luke:** Not to my knowledge. Why do you need to know?

 **Gabriel:** just helping cas out on a mission

 **Luke:** Right! Secret agent man! How is he?

 **Gabriel:** probably not sleeping enough but what else is new

 **Luke:** And you, brother, how is life treating you?

 **Gabriel:** surprisingly well actually

 **Gabriel:** I have a boyfriend now

 **Gabriel:** well its been nice talking thank you for your help bye

 **Luke:** But what about my skittles?

 **Gabriel:** ill have my guy contact you

 **Luke:** And what's this about a boyfriend? Is he hot? Nice?

 **Gabriel:** yes. bye.

 **Luke:** You're so cruel, little brother. My intentions are nothing but pure.

**julikjujubes has left the conversation abruptly**

**Luke:** Aw, OK.

**hellbound has left the conversation in a smug brotherly fashion**

 

 _Well._ That was something.

Gabriel took a moment to process it, chewing another Starburst thoughtfully.

Memory wiping. They could _wipe Cas's mind._

And this Crowley guy sounded like a piece of work. Mind control? Cyborgs?

_Sci-fi nonsense._

 

**julikjujubes began messaging lawboy**

**Gabriel:** sam?

 **Sam:** What's up?

 **Gabriel:** ive got some shit on fergus macdouchewad

 

He relayed the story to Sam, who listened intently and probably began connecting dots all across the board in that over-worked brain of his.

 

 **Sam:** Wow.

 **Sam:** Where did you get this information?

 **Gabriel:** I have my ways

 **Sam:** Shit, Cas is in a lot of danger. This isn't exactly the kind of thing they train for, right?

 **Gabriel:** no I dont think so

 **Sam:** Well, maybe one of us should stop by his workplace sometime. Check things out.

 **Gabriel:** see if hes a little imperio'd?

 **Sam:** Yeah. Also to check out DEAN. That thing is obviously at the center of all this, but the question is, what role does it play? Pawn or player?

 **Gabriel:** dun dun duuuun

 **Sam:** My thoughts exactly

 **Gabriel:** so why dont we make a surprise visit tomorrow for lunch or something

 **Gabriel:** cause if we plan it with him then who knows who from dick corp will be listening

 **Sam:** Good idea, then we can look around

 **Sam:** This is really big

 **Gabriel:** id make a thats what she said joke but this probably isnt the time

 **Sam:** Yeah, probably

 **Gabriel:** this whole thing is just really absurd

 **Gabriel:** I miss not being worried that my little brother is being mind controlled

 **Gabriel:** and I wish I could date you like normal people instead of having this dick looming over us

 **Sam:** Well I'm just glad I get to date you either way :P

 **Gabriel:** what is this a contest

 **Gabriel:** because IM glad I MET you

 **Gabriel:** so there

 **Sam:** I'm DELIGHTED I met you

 **Gabriel:** im absol-fucking-lutely THRILLED I met you

 **Sam:** I'm glad you EXIST

 **Gabriel:** im just really happy being with you

 **Gabriel:** …

 **Gabriel:** sammich?

 

Gabriel sat in a pool of worry for about half a minute before he realized that his phone was buzzing. The contact name read “Sammoose”, and Gabriel fumbled to answer.

“What's up?” he asked immediately, rising from his desk chair.

“I love you.” Sam declared.

“Huh?”

“You're amazing and sweet and I love you.” Sam explained. “Sorry, I didn't really wanna Skope that.”

“Oh.” Gabriel said, falling back into his chair. “ _Oh._ ”

“It's OK if you don't want to say it back yet, but I thought I'd let you know.” Sam continued awkwardly. “So... yeah.”

“Sam.”

“Yeah?”

“Ohmygod. Sam.”

“Yes, that's my name.”

“Wow, snark at me at a time like this. Wow. I'm personally offended.” Gabriel told him. “I... Iloveyoutoo.”

“What?”

“Come on, you heard me.”

“No, seriously, what?”

“Dammit, Sam!”

“Huh?”

“I love you, too.” Gabriel said steadily.

Sam laughed.

“I heard you the first time, dork.”

**Notes for the Chapter:**

> Sabriel fluff between dark revelations :) by the way, my tumblr is lunavocado.tumblr.com if anyone is interested!


	10. Doughnut Be Alarmed

**Summary for the Chapter:**

> Gabriel drops in to say hi, Sam is baffled, Castiel is just done with all this weird. DEAN remains awesome.

“Is there an A?”

“Dammit, yeah.” DEAN sighed as three more spaces got filled. They were playing hangman on Castiel's computer, and Castiel was on his third winning streak.

“Is it 'Acromantula'?”

“Can we play something else?” DEAN asked.

“I'm having fun.” Castiel replied. “You just don't like it because you're losing.”

“No, I'm letting you win.”

“Whatever helps you power down at night.” said Castiel.

“You just got a message on Skope.” said DEAN. “And another one. And a third. Fourth. Fifth.”

 

**julikjujubes began messaging thursdaysgrace**

**Gabriel:** heeeeey lil bro

 **Gabriel:** just wanted to let u know that im popping in for a visit today

 **Gabriel:** no particular reason tho just want to see my favorite non-sam nerd

 **Gabriel:** oh and im bringing sam

 **Gabriel:** just cuz

 **Cas:** This is... sudden? Are you sure this is a good idea?

 **Gabriel:** jeez cant a guy check up on his brother

 **Gabriel:** acquire some chill cas srsly

 **Cas:** Um, alright. Exactly when were you planning on “popping in”?

 **Gabriel:** actually were in the lobby right now if you wanna come meet us

 **Gabriel:** or keep hanging out with your computer friend whatever makes you happy

 **Cas:** You're here already?

 **Gabriel:** yeah sweet digs you got here

 **Cas:** I'll be down in a moment.

**thursdaysgrace has left the conversation**

 

“Dude, your brother brought in a freaking giant.” DEAN, in his omnipresence, remarked.

“That's Sam.” Castiel said, getting to his feet and heading for the nearest elevator. “I don't know _what_ spurred Gabriel into coming in today. I saw him very recently.”

“Well, maybe he's making sure that I'm not going all HAL 9000 on you.” DEAN told him. “Is Gabriel really short, or does he just look like that next to sasquatch?”

“I suppose he's below average height.” Castiel shrugged. Thanks to the presence of DEAN, you didn't have to press any buttons in the elevators. He took you where you needed to go. “This is spontaneous... even for him. I don't presume to know what he's up to, but I doubt he'll make this easy on me.”

“Calm down, Cas. Maybe he really just wants to check in on you.” said DEAN. “I mean, to him, you're the young sibling who needs to be protected, right? There's a sense of duty that comes with being a big brother.”

“How would you know?”

“... I don't.”

Castiel thinned his lips, straightening his back and turning towards the door.

_Ding!_

The doors slid open with a grace to be envied by every set of doors on Star Trek, and Castiel stepped out into the lobby. It was a shining, modern lobby, with lots of uncomfortable couches and stainless steel. The floors were so clean that if you looked down, you could check for spinach in your teeth using your reflection.

“Cas!”

Gabriel practically bounced over, an enormous rainbow lollipop in his mouth. He gave Castiel a hearty _thump_ on the back and as much of a grin as he could manage around the candy. Sam came over too, though he didn't seem to share the sugar high that Gabriel was apparently on.

“Gabriel. Sam. What brings you two here?” Castiel asked, a slight edge to his voice that said “ _do you want to blow my cover???_ ”

“Frankly,” said Sam, “I really don't know.”

“Well, I've been hearing so much about this amazing computer than you're obsessed with, I thought I just _had_ to meet it!”

“Him.”

“What?”

“Meet _him._ DEAN identifies as male.” said Castiel.

“So what? He's a computer.” replied Gabriel, brow furrowed. “I mean, humans, yeah. You don't want to hurt someone's feelings. But robots? Come on, Cas!”

“Cas tells me you cried watched Wall-E, so I don't think you're one to talk about robots and feelings.” DEAN chimed in.

Gabriel blanched.

“Dammit, Cas, spilling my secrets to an AI? Well, when _you_ were eight, you had a big fucking crush on Kovu the animated lion.”

“I was _eight._ ”

Gabriel looked like he was cooking up a wicked retort, but then he glanced at his companion.

“You alright there, Samsquatch?”

“Huh? Yeah, I'm, um, fine.” said Sam, who was looking curiously at the blinking green light and speaker through which DEAN was interacting with them. “This whole hyper-intelligent AI thing's just... a lot to take in.”

“I get that a lot.” DEAN said smugly. “So, hey, I'm DEAN. You must be Sam.”

“Cas mentioned me?”

“He mentioned that you were tall and dating Gabriel. I, being a powerful computer and everything, put two and two together.”

“Uh-huh...” said Sam, still looking a little dazed.

“Gabriel,” said Castiel, “may I have a word with you?”

“Yeah, OK.”

Castiel blinked. He had expected more resistance than that. Nevertheless, he pulled his brother to the side and lowered his voice.

“Really, _why are you here?_ I have this under control.” hissed Castiel.

“Oh yes, I'm sure you do! HQ just wanted an outsider's opinion!” Gabriel said hastily. “I have total faith in you, little bro, but you know how Garrison is. And Naomi just kept _nagging_ at me until I agreed to pop in and say hi. Also, they wanted one of those chips the employees get.”

Castiel narrowed his eyes. He could never be sure if Gabriel was lying. Luke and Michael both had tells. Anna could kick anyone's ass at poker but never told Castiel anything but the truth. Gabriel, however, was a total enigma.

Would Naomi have sent in Gabriel like this? So out-of the blue? Possibly. There were few limits on what she'd do to get her way. And wanting a chip was a very reasonable request, he supposed. But why not just contact him directly?

“Very well.” Castiel conceded. “I'll track down a spare chip. Stay here with Sam and, I don't know, socialize with DEAN or something. I'll be right back.”

“Atta boy!” Gabriel cheered.

Castiel made his way back to the elevators, and Gabriel returned to his little party consisting of his boyfriend and a computer.

Sam looked like a strange mix of baffled, distressed, and fascinated. Gabriel frowned and nudged his a hand, a silent “ _what's up?_ ”

Sam waved him off, but Gabriel made a mental note to keep an eye on him.

“So Gabriel, what kind of brother are you that you never sat Cas down and made him read Harry Potter?” DEAN asked. “It's like Charlie and I have to introduce him to every piece of media ever. Did you know that he doesn't know who Harrison Ford is? What the hell?”

“We had a big, busy household growing up, and I wasn't always allowed _in_ the household, so we may have missed a few spots in his culturing. At least we managed Lion King, right?” said Gabriel, settling into his usual performer persona. “I was a bit of a trouble-maker. Nothing illegal! Well, nothing illegal that I got _caught_ for...”

DEAN laughed. Sam stayed oddly quiet.

“I like your style, man.” DEAN declared. “But jeez, you and Cas are worlds different. It's like, a Vulcan and the entire aesthetic of Willy Wonka were brothers somehow.”

“That's what I've been saying! Cas is from mercury, Luke's from mars, Michael's from Jupiter, Anna's from Venus, and guess where I spend most of my time, Sam!”

“Where?” asked Sam.

“NO.” said DEAN before Gabriel could complete his joke. “Sammy. Think about it. The planet between Neptune and Pluto.”

“... Oh.” said Sam, looking really embarrassed as his cheeks went pink and he rubbed his forehead. “Wow, Gabe.”

Gabriel laughed.

“I'm surprised you didn't catch that one, Samster! You're off your game today.”

“I didn't get much of a breakfast.” Sam explained(see: lied blatantly).

“They've got pecan pie in the break room down the hall.” DEAN suggested.

“Unless it's entirely pecan with no sugar or anything fun, I don't think he'd be interested.” Gabriel stage-whispered conspiratorially.

“Is the pecan pie any good?” Sam asked carefully.

“Oh man, it's the _best._ I mean, I hear it is. But pecan pie is obviously the best kind of pie, so it's stands to reason that it's freaking _awesome._.” DEAN said passionately.

“... uh-huh. I think I'll pass.” said Sam.

“For a moment there, I thought you were gonna burst out into a song about pie.” Gabriel told DEAN. “Not that I blame you. I'd sing about doughnuts if I had any.”

“Break room.” said DEAN.

“Seriously?” Gabriel demanded, eyes lighting up.

“Seriously. No singing, though. There's no singing in Dick Corp.” DEAN told him. “So you're all good down here? I'm gonna check up on Cas.”

“Sure, yes, thank you, go away.” Gabriel told him. “Come on, Sam! Last one to the break room's a broken whoopee cushion!”

“You already have a lollipop. You really want doughnuts, too?” Sam asked.

“Yes. Hell yes. Let's go.”

So they hurried to the break room, and Gabriel found himself immersed in a lovely jelly doughnut. He handed his lollipop to Sam and dug in heartily.

“S' w's up w' y'?” Gabriel asked around a mouthful of jelly.

“Chew and swallow your food, Gabe.”

Gabriel obeyed.

“So what's up with you?” he repeated. “You seem jarred.”

“It's nothing.”

Gabriel gave him a “that's bullshit” kind of look.

“Alright, it's something,” relented Sam, “but it sounds really crazy and I'm probably making a big deal out of nothing.”

“Still wanna hear it.” Gabriel said.

Sam hesitated, glancing around the room. The strange green light was off, so it looked like they were alone.

“I swear to god that DEAN is Dean.”

“Yes, DEAN is DEAN. I'm glad you noticed.”

“No, I mean Dean as in my long-lost brother, Dean.” said Sam.

“Oh.”

“See? Crazy! But there's the whole pecan pie thing, and he talks _just_ like him, and in the same voice, and with the same inflections and slang, and he called me _Sammy._ And it was like I was fifteen again, playing Mario Cart with my stupid overprotective brother.”

Gabriel studied him for a moment, and Sam squirmed under the scrutiny.

“You really think so?” Gabriel finally asked.

“I... yeah.”

“Well...” said Gabriel. “Looks like my brother's getting his memory wiped, and your brother's either a computer, or being emulated by one. I'm not even surprised any more. I fucking _dare_ life to get weirder.”

Sam smiled.

“Thank you for believing me.”

“I generally try to listen to the smartest person in the room.” Gabriel told him, taking a bit bite out of a powdered doughnut. “Or the hottest. In this case, both.”

That actually pulled a laugh out of Sam, and Gabriel felt very happy.

 

**Notes for the Chapter:**

> Can I win the "Least Consistent About Updates" award? This chapter just didn't want to get written! But things are gonna start getting juicy from here on out!


	11. The Fault In Our DEAN

**Summary for the Chapter:**

> Castiel is a petty thief and DEAN has some blips.

Castiel's hunt for a spare chip led him to the very room where he had been initiated: Employee Welcome Room 2B. He shuddered involuntarily as he stepped in, remembering the strange sensation of getting his chip implanted.

The room itself was just as he remembered it – like something out of a James Bond movie. But Castiel didn't know who James Bond was so he had no adequate metaphor for it. And yes, there was a small tub of itty-bitty chips with little wires and stuff sticking out. Castiel honestly had no fucking idea how they worked, but they seemed harmless enough.

He picked one up, holding it up to the light so he could examine it.

“Stealing company property, hmm?”

Castiel froze.

“DEAN.” he said in what he hoped was an even tone. “It's not what it looks like.”

The computer was silent for a moment. Castiel got the strange feeling that DEAN was studying him, deciding what to do.

“You know what, I didn't see anything.” said DEAN. “Just, don't sell that to a rival company, OK?”

Castiel stared at the green light. Could... could DEAN _do_ this? Surely there were codes against letting an employee steal precious equipment! Did Roman set him up to this? There was _no way_ this was a thing that was allowed to be a thing.

“Are you sure?” Castiel asked.

“Yeah. But you should probably scram. Those little things could cause you a _lot_ of trouble.” DEAN said in a lighthearted tone, but Castiel got the sinking feeling that he was deadly serious.

“Right. Um, thank you.”

“Don't mention it. Seriously, don't. Let's go back and check on your brother. I didn't think he'd eat _that_ many doughnuts.” DEAN said, voice following Castiel down the hall and to the elevators.

“He's talented.” Castiel explained, patting his pocket to make sure the chip was still there. His heart was racing – he couldn't place why, but he suspected it was because DEAN was a much more terrifying force of free will than he'd originally thought.

“You're scared.” said DEAN.

“What?”

“Of me. You're scared of me.” DEAN said blankly. “I get your vitals through your chip, remember?”

“Oh.”

There was that silence again.

“I'm not... I'm not malicious software, man.” DEAN said stiffly. “I mean, I have to do as the Dick commands, but I promise that I have no plans to take over everything and enslave humankind. And I wouldn't hurt you.”

“DEAN...”

“No, it's OK. I get it.” said DEAN. “I do. Honestly? _I'm_ scared of me. And I don't mean that in an 'oh, I'm so powerful' way. I don't like what Dick does and I don't like that I'm the one who has to do it. But you're my friend, man. I think that means more than programming.”

“But it doesn't.” Castiel argued. “Programming is what you are, isn't it? Code and HTML and emoticons or whatever, isn't that what defines your basic being? You shouldn't be able to go against that. It's just... not possible.”

“You know what? I don't know what is or isn't possible, but I'm deleting audio recordings of this conversation as we speak, so I'm just gonna take a leap and guess that I can do things a bit differently.”

“Then defy Roman.” Castiel challenged him. “Stand up for your ideals.”

A buzzing noise filled the air. Startled, Castiel clapped his hands over his ears.

“What the hell?” he asked DEAN, but the AI's power light was flickering madly.

And then it all stopped.

“Sorry, what were we talking about?” DEAN asked brightly, green light glowing steadily again.

Castiel stared at him.

“Defy Roman.”

The buzzing and flickering started up again.

“Man, I am _out_ of it today.” DEAN laughed. “What were we talking about?”

“Go against your coding and overthrow Roman Enterprises.”

_Buzzzzzz!_

“Sorry, what?” said DEAN.

Castiel frowned. There must have been some protocol preventing thoughts of rebellion being planted in DEAN's mind. That was smart.

“Never mind.” Castiel said dismissively. “So, can you tell me what the big deal is about these chips? I don't see why every employee needs them.”

“They're very simple trackers, actually, and-”

“If they're that simple, then what's the big deal about me pocketing one?” Castiel asked.

“Oh my god, Cas, you can't just keep bringing that up.” DEAN reprimanded him. “I swear, you're in enough danger already, and- actually you know what, never mind.”

“What?”

“Never mind!”

“How am I in danger?”

“You're not! I just meant that you seem to get yourself into trouble a lot, and I really don't want to regret ignoring your petty theft.” DEAN explained quickly. “I can appreciate a daredevil, but I'd rather my friends not risk their jobs by stealing shit on my watch.”

“You lack the wrists required to wear a watch.”

“My _internal_ watch, Cas.”

“Right. But I don't see how I'm in danger of anything other than losing my job and maybe receiving a moderate fine.” Castiel said suspiciously. “You know something I don't.”

“I know a lot of things you don't. I'm a computer.”

“DEAN, just tell me.”

“I can't.”

“Can't or won't?”

“Dammit, Cas, this is my problem. I can deal with it.”

“First off, it sounds like it's my problem, too. Secondly, even if it somehow is your problem, you're one of us. We watch out for each other.” Castiel replied without a moment of hesitation.

DEAN paused.

“Damn, you just quoted me at me.” he laughed halfheartedly. “Look, I've got things under control, OK? You don't have to worry about yourself, or be scared of me, or anything.”

“I don't believe you. But we can discuss this later.” Castiel said as the elevator went _ding!_

He set off towards the break room, leaving DEAN to flounder in his wake.

“Wait, Cas, you might wanna wait before-”

It was too late.

Castiel had seen the un-unseenable.

Gabriel had Sam pressed up against the counter, and they were making out like the world was ending.

Alarmed, Castiel jumped backwards and slammed the door.

“Of all the things I've ever wanted to see, that was _not_ on my list.” he bemoaned.

“I told you to wait.” DEAN said. “Oh, looks like you startled them out of their tryst. OK, it's safe to go in.”

Castiel took a deep breath and reentered the room.

“Oh, um, hey, Cas.” said Gabriel, straightening his shirt.

“I'm sorry you had to see that.” Sam apologized, somehow managed to tame his hair with a single run of his fingers. “That was... _really_ unprofessional.”

“And hot.” added Gabriel.

“I really don't need details. Or adjectives. Or anything, really.” Castiel assured him. “Look, my break is over, so you two should probably go.”

“Right, yes, we should.” Gabriel echoed, glancing at Sam in a half-lidded sort of way.

In a show of leading them to the exit, Castiel slipped the chip into Gabriel's hand.

“Thanks a ton for having us, Cas!” said Gabriel. “By the way, you guys are low on doughnuts. Nice meeting you, DEAN-o! For a computer, you're pretty cool.”

“Yeah.” Sam agreed. “Pretty cool.”

“I try.” DEAN said casually. “By the way, is that _your_ Impala parked outside? Because that's a no-parking zone and you have a ticket now, but also, _sweet_ ride.”

“It belonged to my brother.” Sam said. “I thought it was time to take it for a spin.”

“Treat that car well. She's a what, sixty-seven?”

“Yep.”

“Awesome.” DEAN said appreciatively.

“Yeah, awesome.” Sam said with a forced grin. Castiel threw him a concerned glance, but Gabriel was already leading his boyfriend out of the building.

“Smell ya later, guys!” Gabriel called to Castiel and DEAN.

DEAN bade them an enthusiastic goodbye as Castiel leaned up against the wall next to the elevator, collecting his thoughts.

“Your brother is a riot.” DEAN told Castiel, any previous tension forgotten. “How did you survive growing up with that?”

“Noise-canceling headphones.” Castiel said, stepping into the elevator after the AI had opened it for him. “Now, about this danger I'm supposedly in-”

The lights went out. DEAN's little green one, the overhead ones, and even the colored buttons.

The elevator stopped.

“ _An unexpected error has occurred with the DEAN system._ ” an automated voice announced. “ _Please wait as we manually restart the elevators._ ”

Castiel's heart sat in his throat the rest of the way up.

“Dude, sorry I blacked out there. I've been fighting a lot of malware lately. Hasn't been easy.” DEAN apologized. “You alright? Your heart's racing like a starving dog for a burger.”

“I'm fine.” Castiel lied. He desperately yearned to question DEAN further, but now they were surrounded by _people_ again. Had... had that been intentional? “Touch of claustrophobia. I feel better now.”

“Oh, OK.”

Castiel returned to his desk and plucked at the little Newton's Cradle that Charlie had given him. He wasn't scared of DEAN – not anymore. Now? He was scared _for_ him.

 

**Notes for the Chapter:**

> In case I haven't mentioned it, my tumblr is lunavocado.tumblr.com - I don't really post anything about iDean, but I post Destiel and stuff.  
> Is it clear that I'm faking my way through computers? I literally have no idea what anything does and it's wonderful and terrible.  
> OK so if it isn't clear, DEAN can see what's going on in all rooms he has access to, but it's easier for him to concentrate his hearing and speech and stuff in one room at a time. That's why he can see what Gabriel and Sam are up to, but didn't hear their previous conversation.


	12. Samson and Dean-lilah

**Summary for the Chapter:**

> Sam should just go to sleep. Really, he should.

Sam Winchester decided that this night would not be a night of sleep.

He sat at his computer, a lukewarm cup of coffee and his dog to keep him company. He was reading different articles about Fergus Crowley, about cyborgs, about Richard Roman, but he wasn't processing much.

Mainly, he was remembering.

All the times Dean had punched people who had picked on Sam as a kid. The times Dean took him to the movies and they laughed at the cheesy special effects together. When they had carved their initials into the Impala. When, rain or shine, Dean had never failed to care about him.

And Sam really hadn't appreciated it enough.

He contemplated calling his mother, but decided that there was no good way to say “hey, your son is a computer.”

Castiel and Sam weren't that close yet.

Gabriel was asleep.

There was really only one person Sam could talk to right now. Someone whose Skope name Castiel had previously remarked upon with a bemused expression.

 

**lawboy began messaging piearesquared**

**Sam:** Dean?

 **?:** who is this

 **Sam:** Sam Winchester. Gabriel's boyfriend?

 **Dean:** oh cool

 **Dean:** wassup sammy

 **Sam:** Well

 **Sam:** A lot.

 **Sam:** But I guess what I wanted to talk about was...

 **Sam:** Do AIs have free will?

 **Dean:** no but i have free willy and free willy three

 **Sam:** -_-

 **Dean:** wow tough crowd

 **Dean:** anyway the fuck i know if i have free will

 **Dean:** do you???

 **Sam:** Touche.

 **Dean:** see the thing about me is

 **Dean:** im a computer

 **Sam:** Shit, really?

 **Dean:** yeah i know its hard to tell but its true

 **Dean:** so basically i make a shit philosopher

 **Sam:** You'd be a shit philosopher as a human, too.

 **Dean:** how would you know?

 **Sam:** Cas has told me a lot about you.

 **Dean:** has he now

 **Sam:** Yeah, he's got a total nerdboner for you.

 **Sam:** Wait, no, that sounded weird

 **Dean:** you use the word boner and expect it not to sound weird?

 **Sam:** Shut up.

 **Dean:** hey, you skoped me

 **Dean:** least youre getting is a conversation

 **Sam:** Here's an idea, how about we don't talk about boners.

 **Dean:** yeah save that for gabe

 **Sam:** Dude.

 **Sam:** If you really want to be discussing my sex life...

 **Dean:** no thank you i really dont want to have to repress another memory

 

Despite everything, Sam found himself grinning. This was the kind of banter he had missed. Nothing ever quite came close to goofing off with his older brother. The smile became a frown, however, as Sam reminded himself that Dean had no memory of who he was.

 

 **Dean:** i mean im not sharing any of my dirty details with you so

 **Sam:** You have dirty details?

 **Dean:** like you wouldnt even believe

 **Dean:** there was that one girl from human resources

 **Dean:** now that was cybersex

 **Sam:** OK why don't we talk about something else?

 **Sam:** Also, I just looked it up. The only women working in human resources are ninety-five and eighty, respectively.

 **Dean:** shit you got me

 **Dean:** wait our employee files are private

 **Sam:** I've picked up a few tricks. An old family friend of mine, Ash, was a computer genius.

 **Dean:** no shit i know an ash

 **Dean:** he was one of my original programers and hes a genius, but wears a freaking mullet and is pretty much a lynyrd skynyrd roadie

 **Dean:** small world huh?

 

Sam stared at the chatlog, thoughts going a mile a minute. When last asked about his current client, Ash _had_ been very evasive... they had chalked it off as Ash just being Ash, but could there be more to it? Sam turned back to the employee directory and looked through it, but found no mention of the man.

 

 **Sam:** Does he still work for the Dick?

 **Dean:** we commission him sometimes

 

That was vague.

Sam picked up his phone and called Ellen.

“Sam, it's two AM. What in the world possessed you to think this was an OK time to call?” Ellen complained after four rings.

“I need to talk to Ash.” Sam said.

“Ugh, alright. You won't be keeping him from anything. That one subsists on about one hour of sleep per night. Let me grab him.”

“Thanks, Ellen. You're the best.”

“Stuff a fork in it, Winchester.”

After about a minute of scuffling and grumbled swears, Ash was on the line.

“Yo, what's up?” he asked, not sounding anywhere near as groggy as Ellen.

“Hi, Ash.” Sam said casually. “Listen, something's come up... you ever worked for Roman Enterprises?”

“Nah.” Ash replied, pausing to take a sip of what was probably beer. “Why do you ask?”

“Well, I'm talking to their AI, and he just described a guy who sounds exactly like you.” Sam told him, frowning. “You wouldn't know anything about that, would you?”

“Nope, sorry. I've tried hacking them before, gave my computer a nasty bug.”

Well that didn't seem right, seeing as how Sam had just accessed their employee directory with only the most basic knowledge of computers.

“Oh, alright.”

“Say, Sam, why so involved? You got an in there or something?” Ash asked.

“... yeah, why?”

“Who?”

“His name's Castiel Milton. Again, why?”

“Never mind. I gotta go. Catch you later, alright?”

“... Alright. Goodnight, Ash.”

“More like good morning, but same to you.”

Sam hung up and thought about that odd conversation.

Meanwhile, it looked like Dean had gotten bored.

 

 **Dean:** hello?

 **Dean:** earth to sammy earth to sammy come in sammy

 **Dean:** huh guess youre busy

 **Dean:** or maybe you fell asleep

 **Dean:** humans do that

 **Dean:** you know what would be a real dick move

 **Dean:** if i played an airhorn sound at max volume from your computer

 **Dean:** i could totally do that

 **Dean:** nah just kidding

 **Dean:** wish i could

 **Sam:** You didn't have to wait for me, you know.

 **Dean:** got nothing better to do dont flatter yourself

 **Sam:** Nothing better to do? Really?

 **Dean:** well actually im procrastinating

 **Dean:** shh dont tell anyone

 **Dean:** supposed to be upgrading our firewall but thats really tedious

 **Dean:** and i might just die if i have to play pong against myself one more time

 **Sam:** Gee, your life is just the worst.

 **Dean:** according to my calculations yes it is

 **Dean:** guess what my calculations also say

 **Sam:** That I'm a bitch?

 **Dean:** yeah how did you know?

 **Sam:** Lucky guess.

 **Dean:** bitch

 **Sam:** Jerk

 **Dean:** look at us we only just met and we're already arguing like an old married couple

 **Dean:** sam?

 **Sam:** Sorry, I got distracted.

 **Dean:** happens to the best of us

 **Dean:** hey

 **Dean:** can i ask you a kind of weird question

 **Sam:** OK, shoot.

 **Dean:** what kind of people is cas interested in

 **Sam:** What?

 **Dean:** you know

 **Dean:** dudes... ladies... both... neither

 **Sam:** I... don't know?

 **Sam:** Why?

 **Dean:** no reason

 **Sam:** !

 **Dean:** no

 **Sam:** !!!!!!!!!!!!!!!!!

 **Dean:** no shut up

 **Sam:** You LIKE Cas, don't you!

 **Dean:** shut

 **Sam:** You LIKE-LIKE him.

 **Dean:** no no no i dont like people i am a computer sammy

 **Sam:** Dean and Cas

 **Dean:** fuck you

 **Sam:** Sitting in a tree

 **Dean:** i swear to god

 **Sam:** K I S S I N G

 **Dean:** jesus christ what are you the worlds most annoying little brother

 **Sam:** I gotta go.

 **Dean:** oh

 **Dean:** ok

 **Dean:** dont tell cas i like him ok because i dont

 **Sam:** Suuuuure you don't.

 **Sam:** Your secret is safe with me. Goodnight, Dean.

 **Dean:** goodnight sammy

**lawboy has left the conversation emotionally**

**piearesquared has left the conversation flustered**

 

“Sammich, what are you still doing up?” asked a bleary Gabriel.

Sam hastily shut his laptop and got up, wrapping his arms around his boyfriend.

“Just some research on that whole DEAN thing.” Sam said. “I couldn't sleep. What about you?”

“I got the most random craving for lemonheads.” Gabriel explained with a yawn, holding up the box. “Come to bed. That wacky computer stuff can wait until it's not the asscrack of dawn.”

Sam heartily agreed.

 

**Notes for the Chapter:**

> That took a while! Sorry. I kinda had to push this chapter, because I feel it's kind of important but it was hell to actually sit down and start it. Once I got writing, though, it was a breeze. It doesn't help that I've got a show coming up, but that's no excuse.


	13. Ashes To Ashes

**Summary for the Chapter:**

> Cas runs into a potential ally, Sam and Gabe have a spat.

“Bye, Cas.”

“See you tomorrow, DEAN.” Castiel replied, exiting the building onto the busy sidewalk outside. He couldn't help the little smile that played at the corners of his lips. Something about that computer just put him in a fantastic mood. Or, on many an occasion, in a terribly frustrated mood.

It was nice, Castiel had to admit, to feel things so sharply again. Or to be frustrated at someone other than his brother. Or to have a best friend.

Because that's what they were, right?

At least, that's what DEAN was to Castiel.

But maybe that wasn't the best idea. There was something fishy going on at Roman Enterprises, and it wasn't just Salmon Saturdays... something told Castiel that things just couldn't stay simple and fun. It was a damn shame, too. He was only just getting accustomed to simple and fun.

Not that Gabriel wasn't fun! It's just that fun with Gabriel was never simple. There was always some sort of scheme or revenge tactic going on. Some undercurrent of negative tension that Castiel had grown accustomed to over the years.

Lost in his thoughts, Castiel had no time to react before he slammed into someone coming the opposite direction on the sidewalk.

“My apologies.” Castiel said distractedly.

“It's all good, man.” the stranger said, rubbing the back of his head and giving half a smile. “Say, you're not Castiel Milton, are you?”

“Why do you ask?” Castiel replied carefully, looking the man up and down. He was pale and scrawny, and wore a mullet. Not particularly threatening, but you never know.

“The name's Ash. Friend of mine said you were having some computer trouble.”

“I'm not having any computer trouble.” Castiel said, brow furrowed. “Mine's brand new, since I spilled coffee on my old one.”

“I meant your _other_ computer, dude.” Ash said with a meaningful look.

“What other- oh.” Castiel said, realization dawning on him. He narrowed his eyes at Ash. “How would you know about that?”

“Call me a family friend.” Ash said casually. “I'm here to help you, dude.”

Castiel considered this, weighing his options. Honestly, DEAN was a mystery Castiel was dying to understand, and this Ash character might be able to help with that. Hell, if he had the right information on the AI, Castiel might have been able to crack what was going on at Roman Enterprises and help DEAN. On the other hand, this guy could be anyone, and Castiel had learned the hard way about being too trusting.

Ash must have noticed this, so he said:

“I'm a friend of Sam Winchester's. You can go ahead and ask him about me, but don't do it over the phone. There's a bit of a security issue. Here, this should have everything you need to know about that kinda computer.”

Ash handed him a USB drive.

“Seriously, dude, talk to Sam.” he told Castiel. “He should be able to help you. Upload that shit on his computer, though. Yours might have some... malware.”

“... right.” Castiel said, still regarding him warily.

“Catch you later, Cas.” Ash said with a two-fingered salute before moseying away.

Castiel tucked the USB drive in his pocket and returned to his car, thoughts piling up like storm clouds in his brain.

On the way home, he rang up Sam.

“Hey, Cas. What's up?”

“Do you know a man named Ash?” Castiel asked, tightening his grip on the steering wheel as his next light turned red just before he could pass through it.

“... yeah, why?”

“I just ran into him today.” Castiel said carefully. Ash had implied that their phones had been tapped, and even if he had been lying, it wouldn't hurt to be careful. “I _trust_ he's a good person?”

“What? Oh, yeah, he's very reliable. I've known him for years.” Sam said, catching on. “What's up?”

“I was wondering if you wanted to come over to my place. Bring Gabriel, too.” Castiel said.

“Yeah, OK. Is everything alright?”

“Just peachy.”

 

* * *

 

“Cas, what's going on?”

“Honestly, I have no fucking idea.” Castiel sighed. He handed Sam the USB drive. “I'm hoping _that_ can tell us.”

“And some random mullet-bearing dude just handed that to you on the street?” Gabriel asked, leaning back in the worn-down recliner in Castiel's apartment.

“Ash is trustworthy.” Sam assured him. “I've known him for years.”

“So this doesn't seem weird at all to you?” Gabriel asked. “For starters, how did he know to ask you if you had a friend in the company?”

“Let's find out.” Sam said, plugging the drive into his laptop.

It opened to reveal a collection of files, labeled things like “BLUEPRINTS” and “all you need to know about dick”. There was also a word document labeled “read this first”, so Sam opened it up.

* * *

 

sup compadres

dr. badass in the house.

you're probably wondering a lot of things right now. i happen to have the answers.

first things first: i have been keeping tabs on that agency you work for, sam. yes we all know about it. it's not hard to figure out and you're as subtle as a brick.

okay so basically, dick co. hired this douchenozzle names fergus macleod to supply them with his latest experiment, and they hired me to write the codes. see, macleod(aka crowley) was more about the physical stuff – cybernetic enhancements and other bullshit-sounding sci-fi stuff like that. he wanted to create what was literally the worst idea i had ever heard of: an ai powered by a human brain.

deal was, crowley would supply the human and i'd supply all the computer business.

(as an aside, i wanted no part in this. the dick's been blackmailing to comply and keep silent – he's threatening the only family i got.)

crowley found what he called the “perfect candidate” - one of my friends, dean winchester.

so yeah

DEAN's dean

*really dramatic music that goes dun dun DUUUN*

so of course this is totally not cool. i've been working for a couple years now on extracting information and stuff on the company, and i think ive finally compiled enough information to a) get the dick arrested and b) rescue dean.

in this flash drive is blueprints, plans, guidelines and everything you need to hold your hand and walk you through unhooking dean and getting the evidence you need to take dick to court.

really wish i could do more but again, he has my family under threat. i can hardly drink a beer without the dick knowing about it.

my advice? write down everything you see here then destroy these files, then storm the castle and save the princess.

dr badass out.

* * *

“... Well, then.” Sam breathed.

“Wait, wait! I haven't finished reading it yet!” Gabriel said, holding up a hand. “... alright, yeah, that's pretty heavy.”

“It explains a lot.” Castiel said, sitting back in his chair. “Honestly, I don't know how we didn't see this coming.”

“It was kind of obvious, yeah.” Sam agreed.

“Why is everything always sci-fi bullshit?” Gabriel lamented. “Why can't things just be normal corrupt things?”

“Well, what are we sitting around here for?” Sam asked, getting to his feet. “Like Ash said – we storm the castle.”

“I agree. This is a game-changer.” Castiel replied, following suit and standing up. “I'll call Charlie.”

“Now wait just a second, fellas.” Gabriel said, holding up his hands. “I know you wanna charge in, guns blazing, but maybe we should take a moment to consider this all-too-convenient piece of information we have, and see if it's enough to handle Dick.”

“Gabriel, my _brother_ is in there, and god knows what they're doing to him.” Sam said darkly. “I can't just wait here and not _do_ anything!”

“We can't just _burst_ in there and ask them kindly to point us to the cyborg, either!” Gabriel countered.

“Um, I'll be in the kitchen.” Castiel interjected awkwardly, holding up his cellphone and leaving the room.

“I wasn't suggesting that.” Sam huffed, folding his arms over his chest.

“Then what _were_ you suggesting?”

“Dammit, Gabriel, if it was _Cas_ in there, we wouldn't even be having this discussion!” Sam told him. “You'd have been the first one out the door.”

“Maybe, but that's not the case here, and clearly _someone_ has to be the voice of reason.”

“Call me crazy, but I can't really see _you_ in that role.”

“Well perhaps you all are being so damn reckless that _I_ seem level-headed by comparison.” Gabriel retorted. “Did you ever consider that Dick is actually a legitimate threat? We step one toe out of line and kaboom! No one ever hears from us again! All I'm saying is we need to _be careful._ ”

“Again, if the situation was reversed...”

“I know, I know. I care too much. That's my thing! And that's why I think this 'storm the castle' plan is a bad idea!” Gabriel collapsed onto the couch, holding his head in his hands. “You and Cas are pretty much all I have, I can't lose you.”

Sam hesitated at this, gaze softening.

“Gabe, Cas is a big boy. He could probably kick both our asses. And I can hold my own when the going gets tough, too. I have a big brother, remember? And it's because of that big brother that I need to do this.” he sat down on the couch next to Gabriel. “And we're gonna think this through, too. I went to college, you know. We're not gonna be dumb about this.”

“I know. You're a genius.” Gabriel sighed. “Fine. Let's light this candle. But if for even a second it seems too risky, promise me you'll back out and rethink your plan.”

“Thank you.” Sam said earnestly, slinging an arm around Gabriel's shoulders. “Really, thank you. This means a lot to me. And I might be able to promise that, but I don't know about Cas.”

Gabriel snorted.

“Yeah, he's pretty into that computer.”

“This is some crazy shit we're in.” Sam agreed. “But hey, if we're gonna be in shit, at least we're in shit together.”

“How romantic.”

 

**Notes for the Chapter:**

> WHAT IT'S FINALLY HERE. I actually updated!!! What!!!!  
> Finally plot stuff will be happening, and it's going to happen SO HARD.


	14. The Majestic Otter

**Summary for the Chapter:**

> In Which Shit Gets Real

“So I'm off work today, tomorrow and the day after that.” Charlie listed. “Wow, what are we even going to _do_ with all that free time?”

“Well, we _could_ sit around the house and you could introduce me to Star Trek: The Next Generation...” Gilda began, eyes twinkling. “Or... we _could_ go to that up-and-coming comic book convention you've been talking about, which I _just so happen_ to have two tickets to.”

“Oh my god.” Charlie breathed as Gilda held up the magic not-really-golden tickets. “Oh my god, marry me.”

“Let's take a rain check on that.” Gilda laughed. “Con first. I believe you mentioned wanting to cosplay Carmilla and Laura with me?”

“You're the best.” Charlie declared, pulling her girlfriend close. “The very best, like no one ever was.”

“To catch them is my very test?”

“To train them is your cause!”

They shared a giggle, foreheads pressed together. Laughter subsiding, they leaned in for a-

_WAITING FOR THE BUS IN THE RAIN, IN THE RAIN, WAIT WAITING FOR THE BUS IN THE RAIN._

“Dammit.” Charlie sighed, reaching for her cell phone. “That's my ring tone for Cas...” she made a face at the phone. “He can probably wait.”

“Go ahead and answer. I'll still be here when you're done.” Gilda assured her.

“Aw, alright.” Charlie moped as she extracted herself from her girlfriend's embrace to answer the phone. Even though she knew he couldn't see her, she adopted her “annoyed older sister” stance and leaned back against the counter. “This had better be good, Cas.”

“Well, um, it's actually the opposite of that. This is un-good.” said Castiel, sounding uncharacteristically bashful.

“So, like, bad?”

“Yes, exactly like that. Can... can you come over?”

“See, I'm kinda in the middle of something over here...” Charlie told him.

“I'm sorry, I really wish circumstances were different...” Castiel sighed. Charlie could faintly hear raised voices in the background. “And it's very unfair to ask this of you. Being fired is the least of my concerns in this situation, and I don't want to put you in a similar place.”

“What? What's going on, Cas?”

“Something big. Dick-wise. You know what, actually? Don't worry about it. Forget I said anything. Sam can handle the technical stuff, I'm sure. The password for Roman Enterprises' wifi is bigdick1, correct?”

“Shit, alright. I'll come over.” Charlie relented. “You owe me big time, alright?”

“Of course, anything.” Castiel promised, sounding relieved. “I'll text you my address, just let yourself in.”

“Got it. Bradbury out.”

Charlie hung up and turned to Gilda, who was watching her with interest.

“Listen, I've gotta...”

“Big important work thing, I understand.” Gilda said with a smile. “Go save the world, the con can wait.”

“You're the best.” Charlie repeated, kissing Gilda on the cheek before pulling her coat on and heading out the door.

 

* * *

 

“Alright, Cas, what's this big important not-good thing that you can't talk about on the phone?” Charlie asked, pushing right into his apartment. That was not Castiel on the couch, however. In fact, unless Castiel had mutated and performed mitosis, _neither_ of these people were Castiel.

“Um, hi.” said the tall guy, who was all cuddled up and adorable with the short guy. Tall guy got to his feet, leaving short guy faking a pout. “I'm Sam Winchester. You must be Charlie.”

“My reputation precedes me.” Charlie replied, shaking his (enormous) hand. “I suppose you're also involved in this big important not-good thing Cas is freaking out about?”

He nodded, lips quirking into a slightly pained smile.

“And your remora?” Charlie asked, glancing at the short guy.

“Hey, if I am any aquatic animal, I am the majestic otter!” short guy protested indignantly.

“That's my boyfriend, Gabriel.” Sam said. He rolled his eyes, but his smile was fond. “Hey, Cas!” he called over his shoulder. “Charlie's here!”

Castiel entered the room, looking more frazzled than Charlie had ever seen him. He gave her a thankful smile and pressed a cup of coffee into her hand, motioning for her to take a seat.

“OK, spill.” she demanded. “What's going on?”

“Well...” Castiel began.

“Wait, we should start from the very beginning.” Sam interjected. “I had an older brother, and he went missing a couple years back...”

“Guy got mixed up with a bad mofo named Crowley.” Gabriel cut in.

“Crowley is involved in some... disturbing affairs.” Castiel explained.

“He makes human-robot abominations.” Gabriel told her.

“And Crowley's working for Dick.” Sam continued. “Simpering and conniving his way into Dick's good graces. Dick, as it so happened, needed an incredibly powerful AI for some reason.”

“Probably atomic weapons.” Gabriel added sagely.

“Crowley blackmailed my friend Ash into helping him design and program DEAN.” Sam said, exchanging a glance with Castiel. “DEAN, as it turns out, is centralized around the brain of Dean, my big brother, who went missing right before DEAN was created.”

“They hooked him up to a computer, mind and body.” Castiel said when it looked like Sam didn't want to continue. “Ash managed to get this information to me, along with blueprints for Roman Enterprises and everything we need to know about DEAN.”

“And these knuckleheads and I are gonna rescue him.” Gabriel sighed dramatically.

“Oh my god...” Charlie whispered, eyes wide.

“But we can't do it without someone on the inside.” Castiel said meaningfully, looking at Charlie.

“Uh, dude, you work there too.” Charlie reminded him dazedly.

“Yes, but I'm not nearly as adept with computers as you are.” Castiel said earnestly, making her blush a little. “You leave us all in the dust.”

“And we can't ask Ash, because his family is under threat.” Sam added.

“And Cas tells us you're super cool.” Gabriel chimed in. “And it's not a party without a redhead.”

“Ain't that a fact.” Charlie replied, still quite shell-shocked. “Um, yeah, OK. I'll do it. Even if I have to miss out on going to a con with my girlfriend.”

“I'll reimburse you.” Castiel said quickly.

“Let's worry about that after we free Dean.” Sam told him. “Since Gabriel brought up the issue of safety earlier, I thought I might call in an old family friend to help us out. His name is Bobby Singer, and he's practically my father.”

“That sounds more than reasonable.” Castiel agreed as Gabriel cast Sam a grateful look. “Any backup we can get is welcome.”

_Ding-dong!_

“Wow, speak of the devil...” Sam remarked, getting up with Castiel to answer the door.

That left Charlie and Gabriel in awkward silence.

“So, um...” Charlie began.

“Yeah, this is a big load of sci-fi bullshit.” he said sympathetically. “Sorry. You get used to it.”

“I don't mind the sci-fi bullshit.” Charlie said dismissively. “It's the least of my worries.”

“Oh?”

“Well, geez, it's like, all my life I've wanted a big adventure, like in Lord Of The Rings or Star Wars or Harry Potter... but now that it's finally come down to that, I don't know if I can handle it.” she gave a halfhearted laugh. “I mean, we could all literally die. Or get arrested. Or brainwashed and turned into a robot. Or die. I already said that, didn't I? And everyone here doesn't seem fazed by it in the slightest, so I'm starting to wonder; am I the only sane person? Or am I just a giant coward?”

“Welcome to the club. We call ourselves, 'Surrounded By Reckless Idiots, Anonymous.'” Gabriel said with a grin, offering his hand for her to shake. “I'm the president and founder. You can be vice president, secretary, and treasurer. We meet wherever evil strikes, whenever we work up the guts to face it.”

“It's an honor, sir.” Charlie replied with a mock salute and a smile.

“Um, well, it wasn't Bobby.” Sam said, reentering the room followed by Castiel and a blonde girl. “Jo, these guys are Gabriel and Charlie. Guys, this is a girl who _really shouldn't be here right now._ ”

“Stick a fork in it, Winchester.” Jo said, hands on her hips. “If Dean's in trouble, then you're not gonna stop me from helping.”

“Apparently, she's been spying on Ash.” Sam supplied. “She lives with him and her mother, and both of them will kill me slowly and horribly if she gets so much as a scratch.”

“Really, Sam? Chickening out on me? And here I thought you were the cool one...” she said coldly.

“Ugh, fine, but if your mom asks, I'm completely against this.”

“Whatever. Alright team, tell me exactly what's going on, and make it in English. I don't speak computer.” she announced, taking a seat.

_Ding-dong!_

“Cas, we _gotta_ get you a more exciting doorbell.” Gabriel sighed.

Castiel rolled his eyes at his brother and got up to answer the door again.

“ _That's_ probably Bobby.” Sam reasoned.

“Oh, so you call Bobby, but not me?” Jo asked.

“We didn't call your mother, either.” Sam replied. “You guys were being held under threat!”

“That's no excuse.” Jo insisted.

“Mm-hmm.” Sam said distractedly as he went to get the door.

Jo looked around the room.

“Uh, well, I'm Jo.” she told them. “I'm here to chew bubblegum and save Dean, and I'm all out of bubblegum.”

“I got you covered.” Gabriel said, handing her a piece of Hubba Bubba.

Sam returned with a brunet woman close behind. She was considerably shorter than him, but her severe expression and the way she carried herself made her seem like the more intimidating of the two.

“Um, this is Jody Mills.” Sam said, rubbing the back of his neck. “I guess she heard about this through Bobby?”

“Like I'd let him keep this kinda thing from me.” Jody said. “This _is_ Operation: Save Dean Winchester's Sorry Ass, right?”

“Yes, although we might go with a different name.” Castiel replied. “Sam, exactly how many more people are we expecting?”

“I didn't know either of them were coming!” Sam complained, running his fingers through his hair.

“Hey, the more, the merrier.” Charlie pointed out. “Remember that Dicks R Us doesn't skimp on the security.”

_Ding-dong!_

Sam groaned.

“I'll get it.” Castiel said sympathetically, heading for the door.

“So I already know Jo and Sam, but who are you all?” Jody asked, gesturing at everyone else. “Last I checked, Dean didn't have anywhere near this many knights in shining armor all lined up for him.”

“Knight? I'm more of a queen...” Charlie muttered.

“I'm Gabriel, the lovable trickster, and the guy who just got up is my brother, Castiel, the socially inept accountant. The vivacious redhead nerd is Charlie.” Gabriel said, pointing at each person in turn. “We're here to put an end to this sci-fi bullshit.”

“... Alright, then.” Jody said.

“-parked out there? Practically screams suspicious. You need t' work on your covert gig skills.” said the man Castiel led into the living room. The man looked around, unimpressed. “Whoever's the owner of the garish purple cadillac, ya left yer headlights on.”

“Oops.” Gabriel said, having the decency to look embarrassed.

“ _This_ is Bobby, guys.” Sam said, grinning and going to give the guy a hug. “He practically raised Dean and me.”

“And clearly I did a great job of that, seein' as how Dean went and got himself all HAL nine thousand and Sam apparently thinks bringing a minor-” he gave Jo a pointed look “-on a life-or-death rescue mission is a good idea.”

“She wasn't supposed to be here.” Sam mumbled sheepishly.

“I can handle myself.” Jo said.

“I'm not saying you can't. I'm sayin' yer mother'll have my head if you get so much as scratched.” Bobby told her.

“Why is everyone so scared of my mother?” Jo asked.

Bobby and Sam both looked like they were about to claim that they weren't scared at all, but Jody cut them off.

“Look, she's here anyway. No sense in bickering. Let's get down to business and deal with family later, alright?” she said. She sat down on the floor, shooing Charlie away when the redhead got up to offer her a seat. “What's the plan?”

 

**Notes for the Chapter:**

> Boy howdy look at all these characters all of a sudden. I should update the tags.


End file.
